Recently I’ve been living next to an illegal and poorly run STR operation and I can now better empathize with folks who strongly oppose them.

You could bring less down and possibly have a lower interest rate since you will be living there.

It very well could become a large enough investment to be worthwhile, also solving for "unexpected emergencies ", for the most part and would an easy self management situation if you were to live onsite in one of your connected townhomes.

Need to see what your market you live and work in presents for these kind of opportunities.. 

You have multiple people living in each others spaces.

The only one this year was figuring out streaming and how to work the Roku. 

I'm imagining something more like add a wall, turn a bedroom into a kitchen-living on one side and a formal dining room into a bedroom on the other side, maybe add a half bath in each unit.

Quote from @Braeden Warg: Thank you for the clarification and information.I live in Cabarrus County and have experience in residential and commercial construction.

The property would be in Florida as that is where I live. 

If they do, you may have a chance under the scenario you're proposing - if they share your concern for it's condition (although that seems unlikely since they've been living with it the way it is for some time, it seems).If you own it, it's pretty lowbrow to expect a neighbor to invest in your property.