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

Could get tight if you go over budget on the repairs.  

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?  

Seller is holding tight on the offer date...seller's market here, but you never know if you don't try.Venturing into loaning money or JV with others though so looking into how that works.

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.  

If you are in a tight margin market, then the thousands of dollars in extra closing costs and interest will eat your margins.