However, I’ve developed some rules for when I utilize a subject to or wrap transactions as both.  

If you’re not well-versed in lease agreements, security deposit rules, or eviction procedures, you could run into trouble.❌ Emotional Stress – Handling tenant issues (especially late payments or evictions) can be stressful, especially if you live in the same building.Hiring a Property Manager in ChicagoPros of Hiring a Property Manager✅ Less Stress & Time Commitment – A property manager handles everything from finding tenants to collecting rent and coordinating repairs.

Also, here's a great article that describes the REPS status:https://www.aicpa-cima.com/resources/article/tax-rules-for-r...And another for the passive activity loss limitation that other mentioned:https://www.irs.gov/publications/p925

There's no fixed max size beyond local zoning rules.

The FHA rules/regs (in particular the FHA self-sufficiency test) are applied the same across all markets, and I know for a fact that in rural communities across the country, and big cities that are not particularly desirable places to live, it's not a deal-breaker, I am not commenting on those areas. 

If you dont have a great team to work with you can lose your shirt even if the house is next door to where you live... there are lots of great areas but only a limited number of great teams so our final choice has always been team driven... saying that we look for an area where there are lots of opportunities  and rental houses available in good areas using the 2 % rule  we found this in Detroit and Toledo  more then willing to share what we do and what we have learnt over the years

The season of Bigger Pockets investors posting 10 nearly identical "Looking for a CPA" messages per day.Disclosure: I am one of those people you are looking for.

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and there's amazing appreciation potential.

When you have studied your market properly you should be able to provide the answer of if single family or residential multifamily is better for cash flow. 1% rule was for a time when almost all deals were decent as a way to rule out the lessor deals and concentrate on the best deals.

A CPA ensures compliance with IRS rules, maximizes deductions, and avoids costly mistakes, especially for higher-income earners with multiple income streams.