That being said, I'm always an advocate for paying for mentorship to fast track your goals. 

Withoutknowing the details I can not suggest which would be right to add on.Several you should pay attention to are:- Ordinance & Law: Provides additional building coverage to deal with rebuilding costIncreases due to changes in Zoning or Building laws- Personal Injury Liability: Libel, defamation of character, wrongful imprisonment, etc.

I think seniors would pay more and be easier on property, but I'm looking at both populations. 

Landlord will promptly respond to Tenant request for repairs but will not be monetarily responsible for tenant disruptions or inconveniences during habitable times of repairs or tenant/guest injuries incurred in or around obvious areas of maintenance, repairs, or construction.We are more converned about them expecting us to pay for their losses rather than getting recouped for damages to our property. 

OMG, please do  NOT take money out of your 401K to pay off a mortgage, especially not for a rental. 

I was looking at an attractive rental but it looks like the land value is 75+% of the value, so I would be paying a ton get very little tax benefit. 

To get a GM, we need to pay a GM wage.

The seller's LLC pays capital gains tax and depreciation recapture, while the buyer's LLC uses the purchase price as the new cost basis.

I'm assuming I would have to pay it off if I won the house. 

If the deal is right you can use hard/ private money to finance the home purchase and some or all of the repairs, then do a cash out refinance to pay off your hard/private money.