We would be able to afford it and live happily ever after, but we would break even on the home that we currently have and lose either 1. 80k that someone else pays/2.a grand every month for life/3. possibly a sale of the house at the $100,000 mark (went for $130k in 2006).

Have the seller do an owner carry for the few grand until you can pay it back.

I am originally from Texas but recently moved to PA (Perry County area) to be around the grand kids.

Fifty-some grand?

I tried that for a while and it was just weird for me, I like to just grab the grand and if they do not close, I am at least 1k ahead.

That's the whole point.I've bought many properties and probates in particular whereby occupant is an heir, a relative, a friend of decedent, ex-partner/boyfriend/girlfriend and grand child's baby daddy and biker buddies. 

You may, in the grand scheme of things, be doing a service for both the seller and investor buyer. 

Then a grand total, that would give me a number that I am "losing" by the property being under market till the individual leases run out. 

I am a STR investor who currently owns two properties in East Tennessee (Smoky Mountains) and I am seeking property in the Nashville area since my son and wife live in Brentwood (south Nashville) and a grand baby on the way.  

I dont hit home runs all the time. i buy on average 4 properties a month here and 1 out of ten I lose money and 1 out of 10 I hit a grand slam.