If it were not needing rehab before someone could move in I would make an offer subject to an inspection and then walk it with contractor/inspector to see where we stood. 

(The front siding of the garage does look crooked, but the overall structure is in a very good shape. has new roof and new trusses ) I only had a week from the date of receipt of the notice to comply.

I just chose from three qualified tenants but one really stood out.

And the other thing that stood out was there isn't a contractors license in Dutchess county.

The first time I used the site, I entered rent amounts that I'm actually receiving for my rental props here in NY, and it was accurate with where my rents stood in relation to what a couple of my next door rental prop owners charge their tenants.

They drank the "STR is the best investment" Kool-aid and bought a decent property, but not one that stood out from the other 20,000+ STRs in the area and did not want to invest money to theme it.Like others have said, I think it comes down to your goals. 

^This way you don't get stood up.

One thing stood out to me in your post, "seller would like to close deal asap", I would do some real due diligence on the building, check with the city building and planning departments and make sure that if ownership changes you can still run it as a bar.

Have you ever looked into adding a garage apt / accessory dwelling unit where a historic garage once stood?  

If the LLC held the property, and you owned the LLC, you still get all the income and tax treatment of a sole proprietor, but the liability bucks stood at the entity level.