I intend on doing a cosmetic remodel prior to selling down the road but it's not ready for that.

The crowd here needs more info on your current financial standing to really give you a road map for success.  

Especially, if 10-15 years down the road we need to change the roof again. 

I can speak from experience as I've had my fair share of S8 tenants.Some have been good, some really bad, and some middle of the road.

It's pretty much a war zone there and I've had to communicate mostly by e-mail and text as cell service is about non-existent, and all the roads are closed so there's no driving over there and no gas even if you did get there. 

If you are buying it for yourself and then renting, the outskirts of Austin, maybe in San Marcos, near Texas State (bigger than UCLA), would be a great place to buy, leverage, and enjoy some nice appreciation down the road.

I have 2.5 acres but would have to be by the road.

What the servicer will do is figure out how much they can squeeze out of the borrower in exchange for kicking the can down the road.  

Kinda hard to tell when someone leaves if they're always on the road anyway (I think I saw him once after they started renting) and I can't be there everyday to monitor the situation and they don't tell me otherwise.

I also hope we have a change in the White House and this requirement disappears immediately.It's interesting that this rule was created the rule to prevent companies from hiding criminal activity even though the vast majority of American companies will never engage in criminal activity.