I have been reading the online resources about getting started, searching the market, and even doing tours, but I am hesitant to jump in and buy a house as I have quite a large amount of student debt.

@Ken M. rents are softening in the places that have had a lot of new units come on line.  

I have just started in a 3-day training for the Lee Arnold broker certification program and thus far just completed the online material required for preparation. 

The auctions, although online now, are live foreclosure auctions, i.e. the auction style sale which is the culmination of the foreclosure process. 

I’m brainstorming ideas on how I can market myself to potential mentors in the STR game in order to gain experience.

In my opinion, an in person meetup > an online connection.You may want to consider making a connection here and meeting up for coffee or attending a real estate networking event.Best of luck!

Looks like a lot of your own capital into the deal, but you learn more from being in the game.

After some research online, I am reading that the cost per square foot on a gut renovation of this nature in Stamford CT is anywhere from $150-$350, which is ultimately not very helpful, because at $150 per sq ft, this is a very appealing project with a total profit of ~$175K (46% ROI) and at $350 per sq ft, it very much isn't, because it would be a net loss of 83K (haha).QUESTIONS:What can I do refine my estimate a bit given that I am not allowed to a formal inspection on the property? 

There's a monthly cash flow 101 game in Bloomington through MN REIA.

Taking action is what separates investors from dreamers.Todd, you nailed it—real estate is a long-term game, and selling a business that’s already producing income is a big move.