Hello, I am currently an 18-year-old entering college who aspires to become an investor later in life yet I understand there's a lot for me to learn.

I completely agree with the other answers that getting someone to help you is a good bet, having someone in your corner who understands the intricacies of the tax code rather than DIYing that should save you more money (and time) than you're paying them ever since I got my first rental I've had a pro doing my taxes but kuddos to you for being able to juggle so much for so long on your own!! 

So often people will want to do an umbrella policy for risk.

Would caution you about trying to be a property manager AND an agent.While they are both real estate related, it's really hard to serve these two different businesses at the same time and do it well.Also, not understanding your lease-to-own goal.

Looking for people familiar with the PR market that can assist with underwriting.

People, particularly amateurs just starting out, tend to focus too much on big tools.

Lending would cease over night and government bailouts would commence.In my area of NE Ohio we are considered disaster free and generally we do not have any of the catastrophic issues that other parts of the country do... welp until last week when three tornados rampaged across three counties ripping down trees, power lines, roofs, siding, and putting over 500k people without power for a week - some still don't have power nor will they until all the trees are removed from the power lines. 

However, most people are not realtors so you do not have access to it.

And also no drama between people.

There are still successful STRs and people are doing it.