I was able to find a local realtor and a property management company to work with and within a month have put an offer on a house!

My grandparents own (2) properties, their primary residence (paid off) and a rental property on the same street (has a bank loan with substantial equity). 

I can also refer you to a few property managers and a contractor I did work with this year that did a great job for me, depending on the size of the project. 

If he's using a 15 year amortization schedule with 10% interest rate it's materially different (economically) than a commercial lender using a 25 year amortization tables and a 5% interest rate. 

If you have a good strategy, and a good plan in place for seeing it through, you shouldn't be worried about anyone's opinion about what you are doing. 

And as stated repeatedly, you shouldn't make a purchase decision based on taxes.

Hypothetically, as a builder / developer, would you pay a slight premium for property that has the federal historic tax credit of 20%, a state historic tax credit of 25% and a city empty building tax credit of 25% - capped at $500,000, as well as a dense mixed use approved PUD, and a tentative $5 mil TIF district for the site?

I've had plenty of great people on paper and a totally different person who shows up.

Would a six month lease with six payments and a deposit up front, transitioning into a month to month agreement be any safer for the owner?

There's a theory that the bronze age collapse several thousand years ago was caused by using something useful (bronze) as currency for a long time, and that thing that was the basis for currency suddenly being less useful (iron invented), leading to all the stores of wealth (bronze, or currency backed by bronze) plummeting in value, and a downward spiral from there.