Nobody flirts with idea of SEC up tail-pipe for the fun of it. 

It's a great idea to think of everything in MTR from the somewhat unusual perspective of the traveler.

I'll echo what Zeke mentioned about interviewing multiple realtors / PM's / Contractors to make sure you can get a good idea of what the area is like, in addition to working with someone you're comfortable with. 

But it gives an idea of the basic considerations and protections you want to have. 

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.

I like both of your ideas so I would look for the single where an ADU is permitted or one with a dump ADU to renovate (that's best) and balance that against the purchase of a 2-4 unit.

@Fakaradin Floyd Your rental arbitrage idea is interesting.

@Rud SevHere is a start:https://www.biggerpockets.com/forums/51/topics/839015-are-sy...https://www.biggerpockets.com/forums/51-tax-legal-issues-con...

You can take a deep look at the deals and get an idea of the kind of variety you'll see and come up with your own due diligence method (that meets your unique situation).

My story, with 1/1000th his wealth (or less.) builds on Jay’s idea of zero debt (I only have a dozen homes worth mid to high 7 figures, but I owe zero.), along with his idea of where you come from and your life experience determines what you need to feel like you couldn’t spend all your money without wasting it.