But I figure I will at least get somewhat acquainted with the area and its community through investing, so I would prefer a place that I like decently enough :) Can someone tell her the damn truth about the reality of OOS investing for complete newcomers?

“But the reality is you work 12, 16 hours a day, and it’s a pretty tough life.”

But stay determined and intentional and you’ll see your dream become reality.

That said, reality is that many states have allowed RE owners (and that includes me, since I own a bunch of rental properties) to pass that cost on to the public.

I'm sure there are stories out there but the fact that I am unable to find such stories, and I'm really really searching for one, tells me there is more motive by attorneys tell us fear stories than the reality actually is.

Again, not trying to be negative or discourage you here, just want you to see the reality from the private money lender's perspective in these "creative investing" deals where the new investor wants to invest entirely with OPM. 

In reality, usually for a few bucks more you can get a unit that will likely be more efficient, won't scream "my landlord is a cheapskate that doesn't care about us," and be longer lasting while still not having all the bells and whistles which are rarely used and likely to cause issues down the road. 

In reality when landlords never raise rents, they also never improve the property.

She couldn't evict because of covid and the squatters trashed the house and sold off all the appliances on craigslist.Local media love to jump all over this and scare you, (that is their job after all) as does any non landlord you tell that you invested in housing - reality is this is incredibly rare and only happens after an extreme lack of competence on the part of the owner.

I am also looking (kinda) but cant see this bubble lasting once the real estate market catches up with reality in Chicago.