Insurance could run me about $80/ month or so. 

For now, you protect yourself with umbrella insurance.

Include a provision about paying taxes, insurance, repairs, etc. to become part of the balance.

Then they are responsible for upgrades, repairs, taxes, and insurance. 

I recommend talking with an insurance broker/risk manager that currently doesn't insure you to tell you the amount of risk you undertake with a pool.

I’d call your insurer first about this

Make sure you have a title search done and get title insurance.

Would it benefit in terms of pro tax, insurance, hoa, utilities (if included in the lease) to be written off?

I am wondering what forum members would do.The house will likely sell for around 155kI owe 55k on first, and 50k on secondMarket rent, is likely around 1250 a month.Roof was done recently, it will need a hvac sometime soon.But other than that its been a low maintenance house.My mortgage payments with taxes/insurance on a 15yr fix at 3.25 percent is 800 a month.I am 5 year into the mortgage, and pay down about 400 a month in principal each month.Thoughts?

The HomePossible loan will likely be a better loan option for you than FHA if you have good credit, and it will save you 1.75% of the loan amount in FHA upfront mortgage insurance premium ($600,000 loan x 1.750% = $10,500 in FHA UFMIP).