Frequently Asked Questions About Real Estate Strategy with Dr. Connor Robertson

1. What’s the best first real estate deal for someone just starting out?

Start with a property you can live in and rent part of. A duplex, triplex, or even a single-family with a finished basement works. FHA loans let you get in with low money down, and you’ll learn how to manage tenants while building equity. It’s the most forgiving learning curve.

2. How do I know if a property is a good investment?

It needs to cash flow under conservative assumptions. I underwrite with worst-case rents, high vacancy, and realistic expenses. If the deal still makes sense, I move forward. If it only works on paper with perfect conditions, I pass.

3. Should I use seller financing if it’s offered?

Yes—if the terms are fair and you understand the structure. Seller financing is one of the best tools for creative buyers. It can eliminate bank headaches and close deals quickly. Just be clear on balloon terms, interest, and default clauses.

4. What’s the downside of short-term rentals?

They’re active businesses—not passive investments. You have to manage guests, turnovers, cleanings, and reviews. If the market slows or regulations tighten, your income can drop overnight. I only recommend STRs in areas where I can legally operate and where I have a strong local team in place.

5. What’s the benefit of mid-term rentals or co-living?

Mid-term rentals hit the sweet spot: longer stays, less guest churn, and fewer city restrictions. Padsplit-style co-living models can produce strong cash flow if done right. You get more income per square foot and still keep operational costs lower than STRs.

6. How should I structure my real estate LLCs?

One property per LLC is ideal for liability protection, especially as your portfolio grows. But many people start with a series LLC or manage through a parent company. Talk to a good CPA and attorney before you scale. The wrong setup can cost you later.