Well over the years I have done 1ks reno/repairs, and I know exactly what the reno will be based on what I am told.

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 own a house now as primarily residence, we are a family of four so that option didn’t cross my mind. 

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.

I had communicated that she could get way more if she let me list it, and I gave her all the options including me paying to get it fixed up for her and selling it.

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 base board heat typical in this area?

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. 

It would give you the best of both worlds: You would pull out some cash to use on another deal and have a strong base of cash flow.

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.