STR feels more like a strategy to break even or eek out a meager return on a great asset than a strategy to cashflow.

That's $1680 per year for QBO, plus my Bookeeper at another $500 a month to log monthly statements, break down loan payments, and reconcile.

It will include an approval letter from the IRS.

if you are going to do things like include utilities, or have an off street parking spot, other amenities etc, there's no reason in my mind you couldn't "charge a premium" for a premium unit/service. 

You’d need to check the local laws to see what counts.Tenant Violations: If they’re breaking lease terms—like not paying rent or subletting—you might have grounds to evict.

One approach that I have not seen included in the discussion is as you are still in the planning phase, you could change your approach and the facts to make it more favorable for your strategy.

I'm also a licensed mortgage broker with a lot of fix-and-flip programs, including some that require as little as 10% down on the purchase price, and provide 100% of the rehab funding.

I guess my goal is to figure out my next steps and get a clearer picture of how I can break into the real estate world and start building something for the future.Thank you.

Not that I'm a proponent of borrowing just for a tax break, but the interest is a deductible expense. 

That can sometimes break usury laws in some states I believe.