@Lexi Teifke Your rental house in Round Rock.

Also, in many residential areas, residents want year round neighbors not tourists; so local pushback can occur there too. 

Mice don't chew perfectly round holes - that was made by a drill.I couldn't possibly get rid of this tenant because then I'd lose all the stories.

STR in those areas do well year round because of fall colors and ski resorts and snow mobiling if they are on a lake, but on the flip side you are paying significant more because they serve dual purpose.  

I'd like to turn it into a year round rental.

Two units are year round, two are mid term.

Just round math use $200,000.  

I'd consider starting with letters then perhaps following up with a few rounds of postcards.

Neither of which are really year round of particularly strong. 

There just isn't enough income left to make someone's world go round.