I am 20 years old and trying to learn as much as i can about real estate so that when i graduate college and have a steady income Ill be able to make smart investments hopefully leading to financial freedom.

This is a great idea that I think I will incorporate.Your point about a contingency line item is smart, I will need to talk to my lender about that possibility. 

But he was smart enough to only take over properties with equity so he was able to refi out of them before the underlying lienholders could foreclose.  

Ditto, I use PriceLabs for my STRs - here is a nice writeup ...Airbnb Smart Pricing Vs PriceLabs: An In-Depth Comparison For Hosts | Boost Your Short-Term Rentals

I am at this point looking an easy/smart way to put something in between.

Probably not; I've done pretty well myself from them, and you're a smart and nice guy so I would be shocked if you *weren't* killing it!

However, the relationship and efficiency of work can be supported with the use of new technology such as AI, can it not? 

Umbrella insurance can be a smart way to shield yourself and your partners from potential risks that basic policies might not cover.From what I’ve heard, local insurance agents familiar with investment properties in your area are a great starting point.

If you were in my shoes, what real estate strategy would you recommend for scaling quickly (but smartly) so that I can replace a good portion of the W2 income from real estate investing?

If selling is your priority, focusing on completing this one first could unlock the equity you need for the next steps.Your idea of forming an LLC is smart, especially if you’re considering investors.