Walk around the outside and look if there are drainage issues, branches overhanging the roof, is the fence sturdy, are there cracks in the foundation.You should be able to get an idea of costs for utilities and taxes.If it looks good, your realtor should walk you through the comps in the area to decide where to start with your offer and what your max price should be. 

It's written rather horribly, so many holes in it, so no it does not detail exactly what denotes "need" nor does it say anything about how long an owner must stay in the property.

The back side shows you the screw holes attached to the trusses.

I have been down this rabbit hole and just want to convey to you my own experience. 

A Bank is effectively the current owner, and even if in your optimistic universe they were to contemplate accepting circa $100k rather than their owed $290k (LOL), such contemplation is likely to take a lot longer than you'd be counting on, meaning that the Contract you would have with the naughty "owner" (whose only aim is to get money out of you), will start burning a hole in your pocket.ie. 

I would help them and yourself by ending it before they get too much more in the hole, assuming that they are going to be paying back the other 20% rent that they haven't been paying.

If it is a total sty you may want to be careful, but if the plumbing and electrical work and there isn't a gaping hole in the side, save yourself 10k and live there. 

There are holes in the shingles at the peak of the roof that you can stick a finger through.

I cut a hole to identify the source and it looks like it was coming from the HVAC (currently set to heat). 

Welcome Matheus,Grab your favorite energy beverage, get comfortable, and get ready dive into the wonderful rabbit hole of Bigger Pockets.