I'd love to speak with any property managers who run properties in the Villages, Florida.

The woman's income covers the bills, and the employer's reference for the man adds credibility.

Or did you run some numbers or have some other set of data you're using to come to the conclusion that Westmoreland County is, in fact, an area conducive to being profitable in house hacking?

And the net cash proceeds are what go into your 1031 account.  

Train with the one thing you have with you all the time FIRST and then go to external weapons if you like.I hear all the time from some 400 pound fat guy they have a gun and go to the range once a week but if they walk more than 20 feet they get out of breath.  

If looking to scale flips and create systems around it to minimize your time and involvement, I'd highly recommend putting a team in place that can handle the day to day operations. 

Quote from @German Sorensen: Feeling the Itch Again: Advice for Getting Back into Real Estate?

You're going to have your signature as a guarantor on the note, so even with an LLC if you default you can be sued for recovery of any shortfall. 

Any tips for a first time investor would be greatly appreciated.

Make vacating the unit a condition to close in your offer.