We should also never have a revenue stream and make money off a tenant's security deposit.

Lot had the dry stream water flow going thru the middle.  

VC Firms and buyers would be looking for a portfolio that doesn't just have 1 or 2 streams of income, but rather also having the direct bookings and social media presence.There may not be many buyers who would purchase a 10-15 property portfolio, but if you scale to 30-50 or even 75-100+ Owned Units, I would think that VC / Private Equity firms may be interested.

Unfortunately, we picked a bad time, because a game just finished, and people were streaming out of Wrigley Field.

So I say, I say “Wait a minute… How come REI supports income streams so much better than Stock / Bond portfolios if it has the same return as stocks?”

You may not get the same tourist volume as Pigeon Forge, but you’ll attract a more consistent, quality guest base.If you're leaning toward an MTR, healthcare contracts and university housing demand will give you a steady stream of tenants.

Assuming you have another stream of income when you move there and I hope you do, I would recommend using the smallest amount of capital possible and invest in the most doors (1-4 units) that you can. 

For example when someone wants to have financial freedom and spend more time with family, but then sets a goal by creating a heavy active income stream that involves their personal involvement daily.

This property would have multiple income streams, including as an airbnb, wedding venue, bed and breakfast, corporate retreat. 

Additionally, creative revenue streams like adding storage or premium amenities can boost NOI.