@Allen Parker real estate is not as liquid as the stock market, so not a good analogy.Also, you're forgetting that the US has a serious housing shortage.The question is, finding areas with shortages that have affordable entry points compared to rents.

I have planned for it as much as one can....I have 500k in liquid cash just to have as a cushion since I am using hard money.

And it was a family affair, very cool.   

Pros:- Everything is all in one place- Easier to manage, less hassle (likely)- More predictable - Easier paperwork Cons: - Less liquid (have to sell all or none) - All eggs in one basket Just off the cuff, those are my initial thoughts. 

That's a cool company name 

You get the idea.Having lots of money tied up in illiquid assets is a recipe for failure if I don't have the liquid assets to overcome a financial hardship.

I think it would be really cool to own an AirBnB in multiple places that I would like to travel to.

The shed is not cool if it really is one, but my guess is it does not have a foundation, so it's no really a building.On the bright side, sounds like you have long-term tenants, which greatly reduces your turnover expenses.

He has strong liquidity and I’m licensed for sales brokerage and I work full time in the Capital Markets space of CRE.

Cool, I got a younger fella out there that is going to start knocking on some doors here soon.