Coming out of finance, I banked profits for a reserve for lean times; yet it still doesn't assuage the anxiety that happens from each booking that cancels.

Yes we could clean ourselves, but elect not to with 3 young kids.In general, all the things that could go wrong for a guest, things that are unacceptable when paying as as a guest (internet outage, clogged drain, etc)The anxiety of managing to positive reviews in the early days when one bad review can do you inUnknown and changing legislation 

It is ok to be scared and have anxiety but don't let it overcome you.

A little anxiety is fine and helpful but honestly you don't need a coach for what you are proposing. 

We were mistakenly given an upstairs unit one time immediately after I had a baby (she was like two weeks old, and our fourth child so we had an 18mo also, and the concrete stairs gave me the absolute worst anxiety) so I agree that a three story walkup won’t be agreeable to her after a few months and she might want to leave anyway. 

I would say if you are a beginner, the geographic distance is probably going to cause you some anxiety over the years. 

You mentioned "not being able to sleep at night" due to anxiety from borrowed money.

I’m not necessarily trying to have immediate cash flow with this, I just have some anxiety knowing that the cities I’m considering buying in will continue to get more expensive and I already have enough for a downpayment so it feels like a waste to not buy sooner than later.

We not only lost our hard-earned money but on top of everything, our health suffered, I had several sleepless nights due to the stress and anxiety that this horrible experience created for my wife and me.After the buy-back was completed, I approached Maverick to at least help us with our losses by requesting us to give back ~$6000.

I can tell you that the stress/anxiety or purchasing an occupied home without seeing it or speaking to the occupants, does not seem to be worth it.