I may be a numbers game. 

Those who know how to play the game can drag things out for a year (no COVID issues). 

I already know real estate is what I want to do after I graduate, and if I start getting familiar with it right now I will be that far ahead of the game when I turn 18.Do you have any tips or ideas of what I can do to get more familiar with real estate?

A pivotal part of the whole plan though is cashing out at some point and I don't like starting out that game $20K in the hole. 

At the end of the day it's going to be a numbers game and I am sure you are going to get more no then yes.

Let this agent help you learn and at least get in the game.

This has worked out great since we can also apply our knowledge of the vacation rental industry and what works best once we are booking the home (themed bedrooms, game room, best bedding configuration and much more).

I switched many years back to a refundable security deposit.Insurance seemed like they had no skin in the game.

EM and due diligence sure thats part of the game  but actually closing we would not do that for what is basically market price.  

You appear to be banking on appreciation, which can be a dangerous game and not something that helps a long term buy and hold investor (appreciation does not help cash flow).For me, without now much information, I would not be interested in the property for anything more than $200k, and that would assume that rents are at market rate and the property is in pretty good condition with little deferred maintenance.