@John SteffenInvesting in house hacking or purchasing a primary residence for rental can be challenging due to affordability, vacancy fear, high interest rates, maintenance concerns, and location analysis.

Any concern for H1B conditions violations?

He needs referrals to mortgage brokers for construction to permanent lending in NY.

Main house is the concern.

This can become a risk for both you and your ability to sell.As for things to talk to HOA about, beyond the permanent exterior colors/finishes, I would also ask about things like dumpsters and potentially port-o-let's that may be needed during rehab.  

This home currently doesn’t have any heat and my concern is bursting pipes. 

Must be on permanent foundation 3.

If your property management involves Appfolio, Stessa is probably one of the only platforms that integrates well.I’m not too concerned about double-entry accounting systems, so Stessa’s simplicity is actually a plus.

Best of luck and feel free to reach out if you have anymore questions or concerns. 

The battery and molestation charges are, of course, the biggest concern to me.