You look like the kind of person who is going somewhere.

(Either with the roofing company, a heloc, or a personal loan.)Either way you will probably be way ahead on interest saved unless you have a sub 6% interest rate.

I personally would fix the 3 windows and maybe consider cutting the rent a little more to gather more interest. 

I'm not a professional Tax person.

Was that person me or another person as that sounds like something I have been telling people? 

The issue was a person sold their home subject 2 and the person who bought it stopped paying.

Personally that is what I wanted, an active mentor. 

So is this just as simple as showing how much the property makes or do they also look at personal debt to income, credit score, reserves etc as well.

If your agent will work for free with no strings attached, that tells me they are either desperate and inexperienced OR they offer a low level of service working many "clients" - either way you lose in the long run. 

I personally haven't sent postcards, I've had good luck with PPC and Video ads.