Your closing costs look reasonable to me based on my personal experience (I'm not an expert though). 

I have discussed this with my contractor and he says that to go over it with vinyl is the best thing (the sellers have just painted it but it is crumbling in several areas) and that he has to wear a full respirator setup like he would for lead based paint abatement or other hazardous materials but just screwing into it doesn’t disturb it so much that it is too much of a problem.

We're based in Florida.

I’m a new investor based in Chicago, but willing to relocate to nearly any city in the Midwest.

Quote from @Nathan Cron: @Michael Evans Hi Mike my name is Nathan I'm a Director for New Western and based in Southern California. 

No offers in this market is typically based either on price or practicality.

“To keep up with annual demand, the US needs 1.86M new homes (for-sale and for-rent) per year through 2033, based on underlying demographics and current undersupply.

Join local meetups, read books, listen to podcasts, find a mentor once you have a base level of knowledge.

You are bidding in the blind based on what you can see from the outside of the house, and (if vacant) what you can see sticking you nose up against a window (usually).  

Uses that also target the business incubator residents/visitors and remote workers might work, e.g. many years ago I'd thought about doing a sort of subscription-based co-working space - something of that sort may do well initially, but may be much more successful in about 5 years as the area continues to redevelop.Current resident population within 1/2-mile is lower-income.