There are a myriad of reasons why, but the risk involved negates any profit potential for a traditional lender. 

Subsequently, I found a reasonably priced unit and proceeded to secure it under contract.

While this sounds great, how does this actually work and does it actually turn a profit?

The City has a reputation of having a strong investment market that draws out of State investors for a reason, but it takes time to learn how to execute it properly.

This may sound crazy, but I own another STR in this particular market, and the reason I think this might actually be possible in based on the value of my other similar property.

Finding available, reliable, trustworthy, reasonable priced contractors is always a challenge.

Well, actually, many jump in without asking a lot of questions, but they get screwed by crooked/ignorant agents, contractors, etc.Many here will recommend starting out by finding a good agent.We emphatically DISAGREE!

I keep telling myself I’m done  What's your reasoning with wanting to stop?

And I think you should ONLY buy in a good area for a variety of reasons, but the main reasons will be the real way you evaluate risk in real estate transactions.Behaviorally, and depending on your goals, it's absolutely asinine to leverage through the gills.

@Aspen Jay, finding the deal is not a reason to expect to pay an agent less.