Is what I want to do legal, is it a thing, and is there a clever way to structure such an instrument where it is legal?

Make sure you get an attorney to draft up all the agreements regarding partnership structure and security instrument for your cash investment.

The best part is the level of automation that you can experience with maintenance tracking.

@James FreeYou could certainly model it out, but practically speaking, I prefer to use the spread between what I can get in public markets vs what I can reasonably achieve on a similar instrument in the private market.

This will cause obvious issues and will take some time to go the automation route. 3) There is a Uhaul business attached to the units that only nets $15k annually.

I say this because, people with full coffers AKA “wealthy people” have more options than most and therefore are able to opt out of owning property (which is one of many ways to financial security) due to the MANY FINANCIAL OPTIONS AND INSTRUMENTS that they presumably have at their disposal.Meaning – instead of buying a $500k investment property, I’ll sink my cash into (gold or silver) for example.

Also- noting for possible devaluations like train tracks, factories, construction, shelters, etc being near the property can be instrumental when analyzing market value. 

My dream is passive income and an automated business that gives me more time to snowboard in Lake Tahoe.Growing up, my best friend's dad had all the time & money in the world because of his investment portfolio. 

There's nothing wrong with that, but it came back so rapidly and consistently that it seemed automated, and that made it feel phony.

My firm actually does this analysis all the time, automated for our clients.