Owner occs will have an easier time getting along day to day, as will those who own something that is safe in all other aspects, i.e. ceiling height, stairs etc. 

Tenant says she’s been without a/c since Sunday (nothing was mentioned of the a/c unit that cools the 1st floor & there’s ceiling fans).

I have seen others I know offer two year leases and at the end of year one offer to do some small updates like new ceiling fans, curtains or landscaping.

id need one too > changing garage door, painting basement wooden ceiling, changing locks etc.

I've been tending to put the bar high, like 78" ( with 9' ceilings I alway build separate storage above) so a second bar can be added, but I think I'll do it your way.

I mean like ceilings caving in and such that you couldn't see on the listing or even a room that looks ok in pictures but not so much person?

I got a bit of a bad feeling when I suggested waiting a year to have the ceilings scraped and she said, "It's best to do them now, before having the flooring replaced, because *something* always gets messed up when ceilings are scraped."

On the walkthrough, the home looked great other than some rotting siding, a couple broken windows, stained carpet and old water stains on kitchen ceiling.

The house is in a solid location but with it being just 2 bedroom the rent ceiling is probably not really very high if you plan to keep as a rental. 

They are simple as long as you aren't installing a fan on a ceiling that can't support the weight.This is probably not going to be your only house project.