The second DOS was in 2020 when I bought enough properties using "subject to" that I couldn't keep up with rehabbing and some sat for a couple of months.

I am a soon to graduate 22 year old student athlete/Husband/Father.

This may change some valuations but nothing will likely be finalized in the next 12-months.I second what Ryan says about the school district drama.

Secondly, how do you finance these units? 

For the second, by "trying" I don't mean that we're struggling to do that but I see why it comes off that way.

The first warning I always do written (via email), second warning is an official letter on their door saying they're violating their lease to allow other residents the right of enjoyment (if you put this in your lease).

Measuring for blinds takes 15 seconds so to go and validate what was said is ok.

If you have your mom live there without any rental income, it is not considered held for investment but is rather held as a second home and does not qualify for 1031 Exchange treatment. 

The second one to build a security net.I've simplified the deal a lot but... am I missing out something obvious?

Second, don't get hung up on what if's.