Admittedly have some emotion attached to it, since I lived there for 15 years.

Although we talk about not getting emotional when investing, it is hard when it is next door to your little slice of heaven.Lower starting price can actually drive it higher in the end.

IMO, and again I just do rentals.. but if I were a buyer... i'd see that as another expense I have to pay... you aren't selling the happy emotions.. you're likely making people see $$$ in how expensive it'd be to pick yours.     

It comes with non-ideal emotional baggage...-- I have some skills in remodeling/construction and some vacation time I could take to do more major repairs/upgrade/etc.The main goal I'm looking for advice is how to go from being a single family house hacker to owning a commercial real estate space that I could art studio hack (share loan payments with other tenants that I manage) to use as a shared art / video /dance studio? 

Also IT HELPS not to be emotional about property.

Unfortunately, I had to explain to him that he put hand-scraped hardwoods in a linoleum neighborhood.It can be emotional, when you're talking about your own home, but I would expect you are asking the question on Bigger Pockets because you want real estate advice.

@Franky Davis also don’t keep trying to emotionally manipulate a engineer.

It would be hard to remove the emotional tie from that investment with me and my family living there.

Sorry to say but business trumps emotions.

Drive towards a solution where you and the tenant come to an agreement and try to remember that he's human...driven by emotional reason.