Note I have 8 digits of local RE and my net worth increases over 7 digits per year for at least the last handful of years.  

IMO self managing is VERY doable for a house hack or for any of your first handful of properties.

That is much lower risk than handing him a bunch of cash and watching him drive away with it. 

So I guess I'm not so much new as I am used to passive, hands off RE investing.

Limited appreciation, old housing stock in need of major capex, population decline in many markets...Can you pick a market that's a couple hours away so the price point is lower, but you can be in-person and hands-on?

Let's give him a hand.

The other party of two, kind of shook their heads, and jogged down a small list of why they don't like them.

Yeah, we do the same, we have a few portable units on hand.

I do that with my IRA, definitely a good option.Technically you can probably do a handful of flips with an IRA, but there’s some fairly steep UBIT and the potential that if you do too much it’s classified as “active income” which is a no-no for an IRA.

There's a handful of active wholesalers on the island that I know and can point you in the right direction, no pressure.