As long as John satisfies material participation test, he can deduct losses against his W2.Scenario 2 + Cost segregation: assuming John placed this property in service in 2023 - yes, he can deduct cost segregation based depreciation.

I recommend connecting with an investor-friendly lender that can give you an idea of what you will be able to afford based on your DTI, credit score, and current income & assets.

The self serve option is hit or miss, I wouldn't use it in a city with strong squatters rights.

. 🤔 Is base board heat typical in this area?

I strongly suggest you hire a PM co, or at least have someone else deal with them for the " day to day " 

If this coach is in your market and knows the key players in the market, has used various property managers and can tell you the good ones, knows the loan brokers, knows the risks of investing on this side of town versus that, knows the tenant base for your area and what they are wanting from their apartments and what they can afford, than I would say a coach (maybe not the one you are interviewing) is worth it.  

Is there a difference based on age or is it based on the age of the roof and the windstorm mitigation done to the house. 

They'll be able to help and point you in the right direction to see if it's even possible to house hack based on your current position and market conditions.

The difference in pre-qualification between base pay vs overtime is significant enough for this to be a deal breaker.

I think that is a decision based on your situation & goals.I'm not sure what your market rates, prices, or demand are, but I'd suggest analyzing both of the strategies you mentioned and see what numbers make the most sense.