A walkable downtown with local breweries, coffee shops, restaurants, etc. 

In my experience, the vast majority of folks on airbnb don't have a clue regarding regulations and are just riding the cashflow train until someone shuts them down.

I don’t see no other restaurants around the area of interest, so how do you go about dealing with comps for restaurants?

By your theory, practically every parent I see in a restaurant is negligent parent because I see their toddler half drawing on the paper and half on the table. 

I used to go to the lunch meeting at Tucker's restaurant on State St.

If the water has been shut off some towns are requiring new lines (at your expense) from their mains to eliminate the lead pipe hook-ups they installed back in the dark ages. 

We had 4 units shut down by a city because of bats.

If you live in Lakewood, which is right next to Edgewater, you are a little further from the Sloan's Lake and all the bars, restaurants, and redevelopment; but the house prices aren't as expensive, and you could probably get pretty close to the same amount of rent per room.

I feel I can offer a lot more in the way of facilitating guest arrival and departure and potentially setting up picnics, tours, reservations for restaurants, ect.

Basically I need someone who could do this for me with regards to taxes instead of just asking something like "do you have have deductions", and not explain common things people deduct or ways you can structure a business to deduct more(like make me wife a part time employee so our meals at restaurants are business expenses).