Figured it would get me good will with the tenant. 

Even if they seem to deal-hoard, there will often be times when they find something they can't act on and will toss it up to the group in good will. 

The lease says "no subletting without the landlords permission" so that is good. Will

I may suggest a delay of onset to October as a gesture of goodwill, but my concern is I am rewarding the behavior of challenging and negotiating my rent increases, and looking for “compensation” for every inconvenience that comes their way.

If none of those, perhaps the call will give you some insight to their timeline and develops some good will rapport with the family.   

Your timeline of 8-10 months sounds good. Will

Everything sterile, pristine, even to the generic pictures on the walls, you couldn't go to a Goodwill and buy something real?

Even though part of me wants to confront him, I'm sure no good will come of it.

Building is 10,000 sq ft and is about 17 units right now. that is made up of:1 apartment16 officesAll updated utilities and mechanicalsFairly large piece of land - 2 buildable lots on itFirst floor: occupied by one long standing tenantSecond floor: remainder of offices - about 5 vacancies - is basically a co-working spaceBeautiful/highly desirable locationNegotiated price is good. Will

I actually found an ozone air cleaner at goodwill, and I use it for a few hours in a bedroom after an airbnb guest leave and it leaves the room having that extra clean smell.