If they plan on renewing they get the convenience of new AC if not you can install the system during your vacancy and your new tenants can just sign a lease for a higher rent (for the AC upgrade) assuming your market commands it.IDK what how big your units are or the building but if they are small enough and space is limited you might consider a Mitsubishi split.

But I haven't personally done that or spoke to my attorney about it and since you are definitely in that space I'll have to take your word on it.

It's not true to the materials, it's inappropriate to the space, and... it just looks stupid.  

I along with all my friends play poker for a living.

We keep them well maintained and tidy with the idea that good tenants want updated, clean spaces and are willing to pay a bit extra for them.Do I let him stay, at least another year until all the other units are turned, or does he need to move on?  

Commercial space usually takes longer to rent so you should definitely weight that into your decision.

The issue is there is water leaking through the walls into living space. 

Exactly what type of space does this project consist of, and what will you be doing with it, demolition and building, remodeling, adding space, changing use, or ?

I have my own inventory of furniture and accessories that I use for vacant spaces.

I own two townhouses in developments with HOAs, but those associations only cover common areas such as landscaping, parking spaces, etc.