You can't avoid it. 

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.

Any counties to target/avoid?

@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.

The compound annual growth rate (CAGR) for 2013-2023 (latest data available) is 5.17%, while the inflation is 2.72% CAGR.Low Crime Rates: Avoid cities with high crime rates.

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?

MLS isn't amateur at all, some of my best deals came from there when I spotted properties that sat too long or needed work others avoided.

Given the situation and the learning curve on my first deal, I’m also willing to give up some profit to structure this properly and get the deal across the finish line responsibly.I’m being careful not to over-leverage the project or eliminate the upside entirely, and I’m also considering an equity partner structure as a cleaner alternative if needed.Completely agree on avoiding unsecured personal debt unless it’s truly a last resort.

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.