In the end, I felt I offered a fair resolution but left with a sour guest who might leave a bad review.

If any of the neighbors sit on the porch and play the banjo, I would avoid that area.

I thought maybe I could play a role by making a nice, comfortable place to live.

Tangentially, there are a fair amount of former STRs now being sold around town in part because of the regs and also saturation.  

Based on my market knowledge, 350k for a new constructions with close to 3k in rent seems like a fairly solid deal for the area.

I see this a lot in the current market, and saw it a fair amount in the down market.  

Finally have enough to consider making a play here and looking to find some locals and read further experiences here. 

I have  water damage in one of my properties in MD, and the IA is playing hard ball.

  * A bonus play would be purchasing a small commercial property with at least a 25 space lot in the aforementioned areas; the idea is to convert the lot into paid parking to increase value.   

When it is a new development, it isn't uncommon to see someone use the date the Certificate of Occupancy was issued - perhaps that marks the "ready", but it still might not be "available".So you can certainly have a property in service in a given year, but not actually have any rental income - but certainly your facts and circumstances are much better if you can actually get a tenant in there, that (should) shore up your defense on that question ever coming up unless you are playing weird games just to get a given in service date for tax purposes.