I don't mind medical bills and student loans much if they show up in credit or are late.

I'm in a less urban area and airbnb and uber have barely made it here.Also, the particular property you describe sounds like it's set up as medical?

@Adam Mazzochi @David Krulac  I think David will agree that Tax sales are very regional.you have tax cert sales  and tax deed sales then something in the middle.. its far more complicated out in the upper east than it is say in CA were I cut my teeth.. in CA its tax deed just like buying a foreclosure.and now a days you bid on line through Bid 4 Assets at most counties.. in the old days you went to the court house and it would be full.. but the bid process was much slower than an east coast tax cert sale.I have been to tax cert sales in MS for example they will sell 30,000 tax certs in 3 days it goes at lighting speed and there is virtually no way to hone in on one property and buy it..Maybe in your area it slows down and you can bid on what your aiming for..

We allowed the father of a tenant of ours to stay a month (as a guest) while he was obtaining medical care at a nearby hospital.

Truth: It’s critical to have, especially Medical.

I do work a bit slower than most contractors, and I usually do the main work myself.

Another potential market would be near the medical center to pick up some of the traveling nurses.

You think you're saving money hiring on the cheap, but slower and lower quality work costs money, too, in the long run. 

I will already be losing some sleep for medical call and am worried about losing the rest (whatever's left) being a landlord.

Her cost of living has very gradually increased (HOA fees increasing, cost of food, medical bills, etc.)