Roof looks older, but still has some life left, no chimney caps, probably needs some tuck pointing.  

I own my rentals outright along with my home, and I have enough money tucked away to weather quite a bit of nonsense.

I also needs some tuck pointing as well and my roof looked at on the status.

@Bruce WoodruffWe found a stack of old playboys from the 80s tucked behind the wall in the basement.

I would Scrape the basement walls, tuck point any loose areas and drylok the walls.  

If you used your investment money to pay the $36,000 you will have the entire cashflow of $500 per month for 60 months = $30,000, but if you get the loan you will be paying out  $230 per month extra for 60 months =  $13,800 extra, or a total $730 x 60 months = $43,800.For 8%, I would play it safe, keep my cash tucked away since it is very difficult to work and save $36,000 in one wad of cash and use someone else's money for such a low rate.

While taking my son to youth baseball, I saw them tucked in re corner and sent the out of state owmer a postcard.

While taking my son to youth baseball, I saw them tucked in re corner and sent the out of state owmer a postcard.

While taking my son to youth baseball, I saw them tucked in re corner and sent the out of state owmer a postcard.

They also tuck them in the door frames.