Gather up all your legal concerns and bring them to an attorney / insurance agent.Ask them at what cost it would take for you to sleep well at night - go with the approach that is simpler and more cost effective.

Having a credible website that you can drive traffic to is very effective.

This however is not as effective on motivated sellers that are specifically looking for "companies", "people" that RELIABLY can buy a house in cash and close within 10 days!

I've had a couple different real estate agents come look at my place as it is now and none of them seem to have any experience with ADU's or had input on how it will/can effect my homes value.

Since you mentioned in Mexico, buyers and renters there want to be in Playa del Carmen, Puerto Vallarta or Tulum so there is a (land) scarcity effect.

All depends on how effectively you can deploy capital - if you can generate higher returns taking the price hit into account, then go for it.

The loan stays in your personal name, so there is some question if just transferring the title has much effect on liability protection. 

But, I reported my profit from my flips under 'sale of business property' and not 'gross income', does anybody have any idea how to report income on tax return to effectively prequalify for the ppp loan? 

3) How does the university effect your decisions?

And it doesn't effect my debt to income ratio's.