You'll lose rent while property is vacant, and you'll probably have to do more repairs to attract a new tenant than you would to keep the current tenant.Is all that worth requiring a tenant to use one specific payment platform?

After this 10 year period we plan to stop buying new properties and aim toward paying off current mortgages to help increase our cash flow in retirement.

If a Room for Rent is worth $1000/month, then reverse amortization at current interest rates between 6.5-8.5% for 30 year mortgage would set the price between $130,000 to $158,000.

-Your current STR seems seasonal, so even without a mortgage, you may not achieve year-round cash flow.

Additionally, we have equity of approximately $145,000.Now, we are faced with a dilemma: should we sell our current property and purchase in a more favorable neighborhood, or should we rent the house and let it pay for itself.We would greatly appreciate any advice you may have.

Property is mid 300's for current value, new build so tax assessor is nailing for maximum, no time lag in assessment being outdated. 

My wife and I are tied to this area due to being in proximity to family and we currently enjoy a farming/hobby farm lifestyle that is a big part of our family culture.

They're currently renting in Denver under only the guy's name but since the girlfriend is pregnant, they need to move to a bigger place.

Currently being leased, but expect my total cash on cash return to be above the number I target.

If you are going to be an owner-occupant, want a low down payment, and are planning to do a renovation, the FHA 203k and Fannie May Homestyle loans are your best optionsHow do you know the property is currently upside down on the mortgage?