Understanding this is a very Tennent friendly state, does anyone have first hand good and or bad experiences in the area renting properties?

The cities he picked are skew towards being "a little more landlord friendly".

If you have a friend of family member near the area, even better.

I plan to hold this property towards retirement as it's in the area I grew up (obviously anything can change).I am receiving conflicting statements from contractors/friends/family on which roofing option to go with.

It's user friendly, with a modern design.

Local meetups. https://www.biggerpockets.com/forums/521Explore Auctions and Foreclosures: Properties in your price range may be available through local auctions or bank foreclosures.Partner with an Investor-Friendly Agent: An agent familiar with BRRRR deals can help you find off-market listings or properties about to hit the MLS.

Skip the vacations, skip eating out with friends.  

Quote from @Joanna Mendoza: Asking for a friend.

For me, I would, put together a prospectus for the STR and approach my friends and family to see if they would be interested in a partnership on it.

@Ian Miller, there is a reason almost everyone starts with people they know: friends, family, coworkers.