How about a  job in the real estate industry both to accumulate capital and gain experience? 

Are there any tried and true/ industry standard sites, forums, etc. where those looking to avoid capital gains look for investment properties?  

The average investor will look at two things: rent and fully impounded mortgage payment.

Also, I've added about $250 to my monthly costs to cover utilities.Looking on Furnished Finder, I do see plenty of places in my approximate price range, so I thought my target (average of $1100/room) was competitive and reasonable.

@Ed Henson REI Nation has one of the best reputations in the industry:)You may also want to look at the Detroit market!

You have a lot of empathy that many in this industry lack.

But you'd be surprised at some of these average smaller towns can do STRs very successfully. 

There is a joke in the industry that anyone who says "I've been doing it this way for (insert number of years here)!"

I hope this give you a better insight as to how the industry works. 

I'd like to pursue sales, and for a while I thought I'd be looking in the tech industry.