What i did not have to do while owning them though was roof plumbing elec appliances stuff like that.. those lasted a good long while..

A long ways from bankrupt. 

Initially, the properties that I buy in another market don't have to cash flow a lot, my metric is $150, as I'm focused on the long term gain when they're paid off  and I have a W2 and am also a realtor.

And , since I had been working in an industry I really wasn’t passionate about, this was my chance to try an industry that I have had a passion for for the last 12 years or so.

Close to a cool little town, close to an area attraction, etc....Also do a search here and see how to screen guests, in addition to what the hosting sites do.... like no last minute bookings, no short stays....

Long term, your property is going to up in value; likely way up.

If you find belongings inside, look closer to see if the tenant has been abandoned or is just gone for a long vacation, hospitalized, in jail, etc.

Since you are already familiar with house hacking, I would consider converting your current home into a rent-by-room or whatever it takes to keep it as a long-term rental, then look for another home you can hack.

I'm in it for the long haul so if it doesn't work on a small scale, it won't work on a large scale. 

If the market continues to appreciate, holding the property could yield more long-term equity gains.