Most of these wholesalers but the bare min in a PSA so you have no recourse.

I get a lot of folks who have income barely equal to the monthly rent, but they still want to see the place. 

True, they may throw off some dividends, but these are minimal in a broad-market index and, at best, relatable to a bond.Real estate investing is multi-dimensional while equities are primarily monolithic - in real estate investing you'll participate in the cashflow, appreciation, and equity growth that you mentioned in your post, while also benefiting from favorable tax treatment. 

I don't cashflow now, and if I move out in the next 2-3 years, I'll only just barely cashflow -- and this is a GREAT deal.All real estate is local.

Originally posted by @Alan Duro:He just desperately wants to make use of this tax loss before he dies (he's in his 70's).I would question why is he so desperate to do so, other than barely on principle "don't want to die with any unopened wine in my cellar." 

"Mental patient released due to Covid terrorizes out of work families barely keeping it together" has to sell somewhere.

I'm sure the best way to learn something is to actually do it, so I'm thinking that participating in some renovation projects in my own home and the homes of families would potentially be a valuable learning experience without the time pressure of needing to get a tenant into a rental property as fast as possible.

The four primary levers (or beneficial aspects) of real estate investing are:CashflowTax benefitsAppreciation EquityYou could start 2 decades from now and still benefit greatly from REI (primarily through Cashflow and Tax Benefits), but your potentially extended horizon means you will participate in each of these areas. 

Should I even bother trying to find people outside of my natural network to live with, because living with someone I barely know might be too much of a headache?

That has been my experience.I know that Bigger Pockets participants talk a lot about taking on debt for investing.