This can be risky as you are not experienced, making it easy to take advantage of you.

You are buying a future stream of revenue, but with some key advantages.

Your approach of starting small, leveraging cash flow and profits from other properties, and taking advantage of opportunities like buying below market value is a smart and sustainable strategy.

The fact that your mortgage balance is relatively low with a 2.375% interest rate is a solid advantage here.

What does it take to get out of that category?

Many states have laws against this, but stop saying you are "helping them out", you are not, you are trying to take advantage of them to sell their home at a discount. 13.

Magaly, you're in a strong position with $100k in equity for each property, and you have a few solid options beyond personal loans to take advantage of.

There will be gaps of course, but I would suggest that you use this to your advantage to max out your rental potential in advance. 

On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

Eventually all that will be left on VRBO especially (Airbnb still has the "rent a room" advantage) is bums on both sides because good guests and good hosts don't need the exorbitant fees and piles of rules.