I keep hearing about the rent to retirement company so I watched their online video.

After securing the deal, the buyer made my wife and I go through three-feet deep of snow to "winterize" the house so there wouldn't be any plumbing issues.It was a 2 hour drive there, and a 2 hour drive back.So much time and effort put into it for only $4k...

If so you could qualify for the 121 exclusion and take the first $250k of the gain tax free. 

So in short, the past six months have been quite an adventure, left my day job, started a business, and moving to AR to start my own path as an architect-developer.

She's been at the property for 15+ years and said it's never been replaced, so I felt this to be a reasonable request.

So many types of companies have traveling workers/guests. 

Thank you so much for your response, Steve.

so just make sure you're not excluding properties because you're looking for 'cash flow.' that's not the point of a house hack, the point is to build equity.off market deals - you can go direct to owner or connect with wholesalers and others that surface off market deals. 

I won't be cashflowing either way (whether I put 0 or 20% down) because of the market conditions, so that's not really what I'm going for (although it would be nice).

You could easily manage that yourself with a handyperson on call.