Then on Reddit groups and elsewhere I encounter young people who seem to believe homes are least affordable ever (not true) and they held these views more than 2.5 years ago when homes in my market were more affordable than most of the last 50 years.  

The most similar scenario I encounter is folks who buy trailers for dirt cheap to rent out here. 60k entry (or whatever they are going for) then 600 a month to lease the pad/land.

Search the BP for ADU appraisals to encounter numerous examples.

Did everything go according to plan, or did you encounter every possible turn of events?

From my perspective, the main issue I encountered is whether you're allowed to transfer ownership from your personal name to an LLC.

Funny is this is the second time I have encountered that in the last 30 days.

And for these newer companies I have to guess they simply have not encountered or planned on failing projects so its all new to them on where what why and how to deal with it. 

Actually RE sales you rarely encounter what you took the test to learn..

While the tenant had a good payment history before my purchase, I'm unsure about their timeliness.Lately, I've encountered several issues with this tenant.

Could you share your experiences if you have encountered a similar situation?