However, I am thinking of having my parents who are retired living there part of the year and doing STR for the remainder of the time.

I'm originally from the area and have been starting to look at some properties there as I am living in New Jersey.

Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

My name is David Burton and I live in TN!

Do these folks have temporary  overage for places to live?

It depends how long you plan on living.

I own a 4plex where I live in one and rent the other 3. 

I bought a single family because I thought I could house hack in the same way as a duplex and in ways it certainly could have and did work but I didn't expect the relational aspects of having people living in a property I purchased.

I tend to stay in my lending and financing lane lol Hi ClaytonMany thanks for the kind offer, Since this is a rental property, my living home insurance(which is way less even though my living home is value about twice the rental property) does not cover landlord insurance. 

At minimum, stage the living room and primary bedroom to give it some warmth.That said, have you thought about cutting bait and putting your money into a market where the numbers actually work?