It’s really about controlling your basis and having a clean path to refinance, not how you funded day one.Some people use all cash because it simplifies execution and avoids short-term debt risk, but plenty of BRRRRs are done with purchase financing, bridge loans, or rehab loans.

I would avoid STR all together in markets that heavily rely on vacation stays. 

He’s helped me think more strategically, avoid costly mistakes, and build confidence in areas where I was previously unsure — all without ever expecting anything in return.

It saves time and helps avoid chasing marginal deals.

In MA, it helps to be a little more structured than that.Here’s what I recommend focusing on:Income verification + pay stubs/bank statements (document everything)Rental history (prior landlord references + payment history)Debt-to-income / affordability (helps avoid issues mid-lease)Consistency across the application (missing info, mismatched dates, etc.)Biggest mistake I see: rushing screening to avoid vacancy… then paying for it later with nonpayment, damage, or constant drama.Always use consistent screening criteria for every applicant and follow Fair Housing guidelines.

That foundation makes future tax years way easier and helps you avoid costly mistakes.Cost seg might help, but it’s not always necessary.

How do I avoid a situation where someone who agreed to work as an independent contractor (for example, on a 1099 basis), works 3 times per week for a month, later claims employee status?

Use that edge to buy conservatively and avoid forcing a rental just to say you own one.If this were me, I’d ask one final question before moving forward:👉 Does this deal still make sense if I treat it strictly as a live-in value-add with a flexible exit?

@Jeff Love Here are the things that many CPAs support their clients with:Understanding tax impact of short-term vs. long-term vs. flip before you buyWhich entity structure is best for goals and investment property typeTax and compliance on LLC or S-CorpHow to transfer property out of personal name into LLC (hard to buy 1st through entity)Ways to optimize taxes throughout the yearHow best to set up accounting to track income and expenses (doing this late is a mess)Feedback on property management systems, accounting systems. systems, etcEstimated payments to avoid penaltiesKnowing when to file and getting things in on timeMaybe a few things I missed, but this is the high-level ….. if you can get answers to the above questions on your own, plan, and file your own taxes then you can avoid the expense of a CPA.

A lot of investors avoid condos because of HOA fees eating into cash flow, but there are good ones if the numbers work.