Yes, absolutely require renter's insurance.

I wonder should I keep it on rent 3500 per month on an average.Property management fee : 300 Maintenance issues: 600 a year on an averageMortgage left: 350K If I decide to sell I might make 700-800K cash.

Is the maintenance of the pool worth the hastle? 

They may require a lease agreement.

Maybe a non-qm lender but unlikely as for owner occupied requirements are very strict for lenders to comply with CFPB.

That said, we're not overly familiar with this market, where to look, or what sort of funds would be required to allow a rental to work.Again, some sort of house hack and MTR strategy would be great but open to suggestions.

Doing it this way would require you to take out the CL in your name and bear all of the risk, but it sounds like you're confident in the numbers so I don't see why that should be a problem.  

You only need a place to track tenant information, payment history, maintenance, etc.

You only need a place to track tenant information, payment history, maintenance, etc.

Physical assets are very much, high maintenance and highly active.