This is the first time I have done something like this, where it was for other reasons besides not paying rent. 

I understand there are many limitations to short-term, or even mid-term rentals down there now, but hoping to see some insights on areas where I might see more of a demand. 

I do / done many rent to own (contract for deed) and a few seller finananced deals where I keep the note.Why not in parallel use a flat fee listing on MLS too?   

Put your “money where your mouth is”.

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?

Sounds like you put in a ton of work to maximize the value, and that basement addition was a smart move.I noticed you mentioned the NYC luxury tax and some of the rental pricing challenges—have you considered expanding your portfolio in markets where you don’t have to deal with those kinds of headaches?

There were some communication learnings on this project where I acknowledged to emphasize expectations.

Quote from @Vince Scipione: Yes, they are a popular choice where I live and work, however with the ever fluctuating cost of oil heat, many people have swapped over their boilers/furnaces to what is called a "Propane Gun" essentially it is a device that is affixed to the front of the furnace/boiler that injects the propane and ignites it.

Plus, I'd prefer to take baby steps before investing out of state where I could better afford a 25% down-payment.

There comes a point where having a real estate-savvy tax preparer outweighs your time learning a new software.