Id have a lawyer on hand, this person seems like they will escalate issues once you notify them you aren't renewing their lease.  

Initially I didn't have a personal connection to the area and didn't know much about the city.

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

If not from the person in office, then definitely from the person running against them.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I am looking at a 5 unit building that I want to do a condo conversion on. 4 units would be vacant 1 has a rent controlled tenant in there who does not want to move. I would owner occupy it so I don't know if I have a...

@Kris Lou Many factors go into PMC pricing:1) Locality (city/state)2) Neighborhood & Property Class (time to manage Class A < Class B < Class C < Class D)3) Property condition (slumlord properties hard to manage)4) Number of units (some economies of scale, but not as much as owners think)5) Owner expectations (some owners really want a personal assistant!)

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

You’re still going to be personally sued when something goes wrong. 

One of them I have used personally.