The issue is this, the house has 18k in taxes due and they don't wont the hassle of paying the taxes, they don't want to be a landlord because of their ages and they do not want to lose the house.

Congratulations on your first step towards your goals at such a young age, you're off to a good start!

Hey Sam - welcome to BP and congrats on getting started at a young age!

The age of both buildings is similar, so I suppose that should tell me something :)The seller will "redo" the roof as part of the deal, but that really just means re-apply the waterproof coating.

Must be over 21 years of age.

IF you just avoid the protected classes you should be fine - age, race, religion, etc.I have in depth conversations with renters to get to know them better.

Mostly jeans, work boots etc, middle aged working class from what I notice touring that neighborhood.One concern is the lack of documentation/ non-notarized.

Depending on the sizes, ages, conditions, and demand, the price and terms will very when you resell them.If you do have to move the homes then this changes things considerably.

I would like to take an aging house, force some equity and cash flow it.  

At our age it seems silly to have taxable investments, since 59 1/2 is soon.