The chances of it closing were probably on the low side, and jumping through the REOs hoops could have been the real deterrent.

I hope I'm wrong because I'm rooting for you, but most seller's are going to balk at things you should have noticed during your initial walkthrough especially if you are asking for something big like the roof (which probably also visually has buckled shingles or other indicators that it's at or close to end of life)A credit at closing is the same as cash to you because it's money you don't have to put into the title company.You will ONLY get a cash return doing it yourself.Exposed Romex is $25 to replace with conduit and a surface mounted box if you do it yourself.

These are hand picked and visually raked, so some of these have never been contacted. 

Aside from price, bad photos can be a deterrent for potential tenants.

These are hand picked and visually raked, so some of these have never been contacted.

For me, I need that visual reminder on a daily basis.

Therefore, I am not sure wear should be that big a deterrent against sublease.  

I’m having a hard time visualizing all the debt I would take on with Helocs, etc.

Your market will largely dictate this, but I know in my market here in CT it can be a potential deterrent to landing good tenants. 

The condo I am thinking of getting can only be rented for longer than 1 month, should that be a deterrent?