Based on your explanation, it looks like I fall into category 1 since I plan on repeating this strategy at least 2-3 more times.  

As an investor, I've seen far too many people allow their emotions get the best of them and fall into that trap.

There is obviously a formal lease, and we also supplement with a room mate agreement which outlines the more specific things like overnight guests and expectations in dispute resolutions/ cleaning/ care for the home and appliances, etc.I haven't received one formal "LL request" email yet, other than a formal 30 day notice in the event of a move out, which is usually after they've come talked to me in person about it to begin with. if there's an issue, it tends to be pretty limited to "hey, we have this shower rod falling off"... which im usually here to deal with (and tbh most of the time they like to fix it up with me), and it doesnt need to turn into a big thing. as for keys, i have the house on a yale smart lock, so 'handing over keys' is just official move out, walkthrough of the room for damages, and then I can delete their access code and access to the smart home systems without having to re-key the house. 

You would also benefit from a ranking software like Rankbreeze or Intellihost which would also show you the pricing of your comps and where you fall in the rankings of the OTA.

I work with all the big box lenders and I have worked with a private hedge fund and I have worked with smaller, local HM outfits and NONE OF THEM had anything like that.Because if the deal falls apart I am guessing they keep your 2500.

Multi-Family apartment buildings 5 or more units are zoned Commercial and therefore fall under commercial loan guidelines.

I have comped it myself and it falls in line with what it is appraised for.

.* Spread the Risk - As interest rates rise and fall, having three mortgages spaced out will reduce your risk. 

I had an existing business fall to pieces and am in the process of looking for a job (or other means of income), so money is hard to come by. 2.

Are rents rising, falling or flat?