Building Your Real Estate Dream Team – The People Who Make Investing Possible
Why Having a Team Matters
Over time, I’ve learned that the success of your real estate investments is only as strong as your team.
Behind every successful investor is a trusted, reliable group of professionals who help them find, evaluate, finance, renovate, and protect their properties. Whether you’re house hacking your first home or expanding your portfolio, the people you surround yourself with can make all the difference.
Without the right team, real estate investing can feel overwhelming. But with the right people in place, everything gets easier from finding opportunities to solving problems to scaling for long-term success.
The Sarah Lee Living Team at a quarterly meeting.
1️⃣ The Mentor: Learn From Someone Who’s Done It
Before you build your team, find someone who’s already done what you want to do. A mentor can offer perspective, share lessons learned, and help you avoid costly mistakes.
I’ve found mentors in many places through family connections, introductions from business relationships, conferences, and masterminds. But one thing has been true in every case: each successful mentorship began with delivering value to that person through some act of service. By helping them solve a pain point or achieve a goal, our relationship became a two-way street.
The lessons I’ve learned from my mentors over the years have gone far beyond business they’ve shaped my mindset, priorities, and approach to life. These relationships have become some of my most treasured and meaningful connections.
💡 The best mentors remind you that every successful investor started small and progress is built one property, one lesson, and one relationship at a time.
2️⃣ The Realtor Who’s Walked the Walk: Your Trusted Advisor
Your realtor is one of the most important people on your team and if you’re investing, you need someone who thinks like an investor and has the experience to back it up.
I call this person a “realtor who’s walked the walk” because they don’t just study real estate they live it. It’s helpful if your agent has personally invested in property themselves. Some things are best learned in the trenches; books and classes can only take you so far. There’s no substitute for real-world experience when it comes to navigating the nuances of deals, renovations, tenants, and negotiations.
I began investing in real estate in 1998 but didn’t get my real estate license until 2015 so for almost 20 years, I relied on third-party agents to help me find, negotiate, and close deals. Spending time with my agent became a weekly (sometimes daily) occurrence. We reviewed thousands of properties on paper, toured hundreds in person, refined our “buy box” for each portfolio, and spent countless hours driving through neighborhoods together.
Over time, we reached a point where we could finish each other’s sentences. Through trial and error, we learned what made offers most competitive and how to position them for success. Those professional partnerships turned into treasured friendships, and even today, as a licensed realtor myself, relationships with other investment-minded agents remain a critical component of every successful deal.
💡 A realtor who’s been in the trenches understands the highs, the lows, and the strategy behind every purchase and that kind of wisdom is worth its weight in gold.
3️⃣ The Lender: Your Financing Partner
Your lender is one of the most important financial relationships you’ll ever build as a real estate investor. A great lender doesn’t just fund your deals they help you strategize, prepare, and grow. Over time, you’ll likely have two types of lender relationships: one traditional and one less conventional.
The Traditional Mortgage Lender
This is the person who knows the ins and outs of conventional loans, FHA, and VA products. They’ll help you navigate the process for your primary residence, a house hack, or even a second home purchase.
A top-notch traditional mortgage lender will:
Understand your goals for real estate and your long-term financial plan.
Keep an updated file on you refreshed every six months so you’re ready to move when the right opportunity arises.
Connect you with people in their network who can help you grow.
When you’re buying your first few properties whether it’s your personal home, your first rental, or your first house hack this will likely be your person. They’ll help you take advantage of the best loan terms available while positioning you for your next step.
The Local or Portfolio Lender
As you grow, you may also form a relationship with a less conventional lender often someone at a community bank who understands the business side of real estate investing.
These lenders typically offer in-house loan products or “portfolio loans,” meaning the bank holds and services them rather than selling them to a secondary market. They can often offer more flexibility things like renewable 36-month notes, lines of credit, or guidance lines that give you access to capital quickly when an opportunity arises.
Just like your traditional lender, this person should also have an updated file on you your current properties, financials, and goals so they can act fast when the time is right.
Real Relationships That Matter
These folks are critical members of my team a short list of trusted conventional lenders and my go-to “in-house” lender at our local bank. I have these guys on speed dial. I know their families, and they know mine.
We meet regularly over lunch or drinks to share market insights, talk through updated plans and goals, and make sure we’re ready to tackle the next deal when it comes around. Real estate may be about numbers, but success always comes down to relationships and my lenders are among the most important relationships I have in this business.
💡 Your lender relationships should evolve as you do. Start with a great mortgage lender who helps you buy right then build a partnership with a local bank that can grow with your portfolio.
4️⃣ The Home Inspector: Your Eyes Before You Buy
The home inspector plays a critical role in the due diligence period and a thorough inspection can literally save you from buying a money pit.
Educate your home inspector about what matters most to you in a property so they understand your priorities. If your focus is on long-term rentals, they should be checking for the systems that make or break a good investment HVAC, plumbing, electrical, roofs, foundations, and water intrusion.
When I first got started, I had one inspector who became a trusted part of my team. He knew exactly what we were looking for in a purchase because he had inspected so many of our properties over the years. He knew our standards what repairs we were willing to take on and which ones we would walk (or run) from. When he came to inspect a new potential purchase, he already knew the context and the criteria.
Your home inspector can also serve as your reality checker the person who keeps you from making an emotional purchase because you’ve fallen in love with a house. A great inspector helps you see things clearly and objectively, and if you let them, they’ll save you from costly investments that don’t align with your goals.
💡 A great inspector doesn’t just find problems they help you make informed, disciplined decisions before you buy.
5️⃣ The General Contractor: Your Renovation Partner
As you grow and begin investing in more distressed assets that require renovation, having a very experienced general contractor becomes a must.
I’ll also say this buying heavily distressed properties that need major renovations probably shouldn’t be one of your first five purchases. The rental business is complex enough with many moving parts; adding the challenges of a full-scale renovation introduces another layer of complexity you want to be fully ready for.
When you are ready, a great general contractor can make or break your success. They should absolutely be involved before you purchase the home as part of your due diligence team and in some cases, for major renovation projects, this person may even take the place of your home inspector.
A top-notch GC will:
Help you evaluate the property before purchase, providing realistic estimates for renovation and repairs.
Identify which improvements are essential versus cosmetic.
Work from your defined renovation scope and standardized specifications using the same toilets, water heaters, HVAC systems, light fixtures, appliances, and paint colors across your portfolio. The more you can standardize, the easier it becomes to maintain and repair your properties over time.
So how do you find the right contractor? Start with trusted referrals. Ask your mentor, your portfolio lender, or other experienced investors who they use and trust. When you get names, do your homework get references and actually talk to them. Visit job sites or completed projects in person photos and videos can be misleading. You want to be 100% confident in this person’s skill, reliability, and integrity before you bring them onto your team.
Be sure you’re factoring all expenses into your CapEx (capital expenditure) budget and always include a contingency allowance for the things you might miss during underwriting. Renovations have a way of uncovering surprises, so plan for them from the start.
💡 Some of my best deals are the ones I didn’t buy. Knowing when to walk away is just as valuable as knowing when to take on a project and having the right contractor on your team will help you make that call with confidence.
6️⃣ The Property Manager: Your Operations Backbone
Property management is such a critical role and there are so many ways to approach it that I’ve dedicated an entire blog to the topic. Be sure to check that one out!
In the context of this blog, I want to reiterate how important the property manager role is on your team and why this level of expertise should weigh in on every real estate investment you evaluate.
Even if you plan to self-manage, involve a professional with heavy experience and detailed knowledge of the local area especially from a rental perspective. This person should be extremely well versed in current rental rates and able to provide you with recent rental comps. They should also have a solid understanding of local zoning and neighborhood nuances that may impact your property’s long-term use or performance.
(Side note: If a property is in a subdivision with an HOA, you’ll absolutely want to speak directly with the HOA manager to learn firsthand about any rental restrictions in that area. Depending on the market, it’s also a good idea to confirm zoning and local ordinances this is especially important if a potential future use could be a short-term rental.)
In my experience, it’s always best to be conservative especially if you’re upgrading a property and expecting to achieve higher rent than it currently generates. The expected revenue from a property can make or break a deal, and you want to be sure your numbers still work below your best-case scenario.
A strong property management professional should also be able to help you estimate your annual expense budget not just general expenses and maintenance, but reserves and recurring costs like taxes, insurance, and management fees. This level of insight helps you build a realistic pro forma that accounts for both income and operating expenses from day one.
It’s also smart to model every deal with property management fees, even if you plan to self-manage at first. You don’t want to be tied to a property just because it only works financially if you handle everything yourself.
💡 Great property management creates freedom and that’s one of the biggest rewards of investing.
7️⃣ The Handyman: Your First Line of Defense
Your handyman and yes, I’ve worked with several incredibly talented handywomen over the years is one of the most critical members of your real estate dream team once your properties are up and running.
Unhappy tenants or properties that fall into disrepair can quickly turn a great investment into a nightmare. Your handyman is both your first line of defense and your preventative maintenance person. Having them put eyes on an issue helps ensure the “right” repair is done the first time and that can save you a lot of money over the long run.
Doing small, repeated repairs without addressing the root cause can be a huge drain on your annual property budget. Sometimes, the right repair is the more expensive one and your handyman should help you evaluate that.
In our portfolio, we schedule seasonal maintenance twice a year once before it gets cold and once before it gets hot. Our handyman follows a detailed checklist that includes changing HVAC filters, checking smoke detectors and fire extinguishers, cleaning gutters if needed, inspecting under sinks for leaks, and doing a visual inspection of the property with photos. This proactive approach prevents small issues from becoming costly problems.
It’s also helpful to negotiate rates with your handyman as your rental portfolio grows. Over time, as you give them more consistent work, your negotiated rate should reflect that partnership. That said, be fair in how you compensate them this person is the eyes and ears of your operation, and you want them to feel valued and respected.
Be organized in how you manage this relationship. Use work orders and photos to document repairs and have them invoice by work order. Keep all maintenance records digitally so your property management team can access them easily. We use Dropbox and Propertyware to stay organized and transparent.
⚠️ Important Side Note:
Your handyman should not replace your own eyes and ears. Plan to visit your properties attend a few seasonal inspections yourself. If you’re facing a potentially major repair, go with your handyman to evaluate the situation. Sometimes your handyman is the right one for the job, and other times, you may need to bring in a contractor with more bandwidth or specialized skills.
I’ve learned this lesson the hard way it’s important to use the right tool in your tool belt to solve every problem, both for cost and efficiency.
💡 A great handyman doesn’t just fix things they help you protect your investment, your tenants, and your peace of mind.
8️⃣ The CPA or Tax Professional: Your Financial Strategist
If you want to make real estate part of your long-term wealth strategy, it’s important to choose a CPA who is well-versed in the ins and outs of real estate investing and how to use real estate to mitigate taxes.
This is not every CPA’s strong suit and having someone who truly understands real estate can make all the difference. The insight and guidance this person provides can help you:
Structure ownership properly for the most tax-advantaged setup.
Time your purchases and sales strategically to minimize tax exposure.
Utilize cost segregation studies to accelerate depreciation and offset income.
Employ 1031 exchanges to defer capital gains taxes and continue building wealth.
A knowledgeable CPA can also help you understand what expenses you can write off as an active real estate investor, what you should be tracking (and tips for tracking it easily), and how to stay organized from an accounting perspective at every stage as your portfolio grows.
This system may evolve over time but the bottom line is, you need an organized framework to ensure you’re maximizing both operational efficiency and tax benefits.
As with so many of the professionals on my dream team, my accountant isn’t just a service provider she’s also a trusted friend. We’ve spent many hours together often over cocktails talking strategy, reviewing plans, and making sure my tax approach aligns perfectly with my overall goals.
💡 Your CPA isn’t just about compliance she’s a key part of your long-term wealth creation plan.
9️⃣ The Insurance Agent & Attorney: Your Protectors
Once your property is up and running, you need to protect it and that’s where your insurance agent and attorney come in.
I’ve used the same insurance agent for the past 15 years, and this relationship has saved me hundreds of thousands of dollars and given me incredible peace of mind. When a tree falls or a house catches on fire (yes, we’ve seen it all), you want to be absolutely sure you’re properly insured.
Your insurance agent should be involved before you ever purchase the property during the due diligence phase to help you estimate and budget for your insurance premiums. This ensures your coverage is in place from day one of ownership, not after the fact. Property hazard insurance rates have been rising steadily over the past several years for a host of reasons, and your insurance professional can help you stay informed on these trends so you can build accurate forecasts into your yearly operating budgets.
Because this topic is so important and can make or break your financial stability as an investor I plan to dedicate an entire blog post to insurance soon, so stay tuned for that.
Your attorney is also a critical part of your team. As you begin to invest more, you’ll want to have a relationship with a preferred closing attorney who understands your business structure and investment goals. They’ll keep your corporate documents organized, know your closing preferences, work in partnership with your lenders, and ensure things run smoothly from contract to closing.
💡 The right insurance agent and attorney protect your assets, your investments, and your peace of mind because no portfolio is complete without the right protection in place.
Bringing It All Together
Real estate investing is a team sport. Having the right people in your corner makes the process smoother, safer, and far more rewarding.
Start building your team early before you buy your first property. Your agent, lender, inspector, contractor, and property manager will guide your first deal, while your handyman, CPA, insurance agent, and attorney will help you protect and preserve it.
As your experience grows, so will your network and that’s when the magic happens.
Final Thoughts
If you’re thinking about buying your first investment property (or even turning your current home into a house hack), now is the time to start assembling your real estate dream team.
At Sarah Lee Living, we’ve built strong relationships with trusted professionals from lenders and contractors to inspectors, handymen, and mentors who share our values of service, excellence, and integrity.
Because at the end of the day, real estate investing isn’t just about properties it’s about the people who help you make it happen.
👉 Ready to start building your team? Let’s talk about how we can help.
