What I've been considering is installing a few "smart outlets" (outlets with usb plugs as well), a dishwasher, a garbage disposal in the kitchen sink, new LED light bulbs throughout, and some light caulk work. 

I want to lock the property under contract then wholesale it to a serious investor.I want to make sure I use a valid purchasing agreement and assignment contract.

If I could save up $5000 by graduation do you think it’d be smart/possible for me to get a loan on a house?

@Blake Edwards I was using smart move for all of my Berwyn properties, but I recently switched over to Zillow.

All of those will go off of your purchase price on the contract. 

Literally my only issue with living in this house is the section 8 neighbor…I got the Mayor to send some people down to police the place and they calmed down but I had a house under contract right before that happened and ended up moving anyways.TL;DR: Should I shell out 8K to fix the roof on a house with currently minor and fixable leaks but with a roof that needs replacing soon, or should I just move again and risk having to put up tarps if it leaks this winter (Seattle).

If they were smart, they would see that they're paying my mortgage. 

Be smart !!

As a result, the smart REI investors are looking for B-minus or C-on-the-borders-of-B areas.Fountain Square is the neighborhood where a lot of REI's [including ME] are trying to find properties - thanks in large part to HGTV's "Good Bones". 

I’m under contract on a property in Indiana.