My one concern with the deal is that you say that one side has been completely gutted.

Asset protection becomes a major concern if you own a bunch of free and clear properties here.You sound like you've recently dealt with some estate matters, but the question of your heirs and their ownership interest in any of your assets come to mind as a concern. 

My biggest concern is that I just paid off my student loans and don’t have the cash flow to put down any money on a property right now - I also thought it might be better to own a home before starting in order to get some real estate experience on the home buying side.

I guess my initial concern, since I'm already incorporated, is how do i get listings up on MLSLI. 

My only concern with the health share plans is it seems they all have some sort of "disclaimer" clause that basically says at the end of the day, they don't have to cover an event if they don't want to.

The concern is we already have a vacation home in the same area that we're thinking of selling and we don't want this new one to be considered an investment property.

I don't really have 3 favorite improvements to add value to my properties as far as appraisals are concerned. 

However, I think it's appropriate to have a minimum for all concerned.

One concern is this:  No other owners in Old Louisville have modern, trendy, updated units so theres no proof of concept.  

The only concern I have about new construction is the new property tax value when completed.