Benjamin,
I offer a question, why not do both? Consider taking community college classes toward a business or real estate degree to keep the cost down. There is nothing stopping you from also working while in college and possibly working toward an career in real estate. Either way, you will have multiple options. Why tie yourself to only one or the other option, when you can have both? You seem very smart and ambitious, put that ambition to work for you. Give yourself as many options as you can in life. You may not quickly find that $20k investment that lands you$1k per month, so why not have a backup plan (yes, a college degree J.O.B.), that can make you as much money as possible until you do find it?
If it helps, I had the same thoughts many years ago at your age. I got a four year degree in Computer Science, and have always been glad I did. I paid for it on the ten year payback plan, so no silver spoon. And no, I don't still write computer programs, and haven't for years. I also built my first house at 19 yrs old, while in college. It wasn't easy. My parents thought I was crazy, and I'm sure they had a few sleepless nights over my eagerness to succeed at such a young age. I now also own a good number of rental properties, and have been successful at both a J.O.B. and REI. I learned many hard lessons over the years, but was never sorry I went to college (or that i got into real estate at such a young age). My point again, give yourself as many options in life as possible. You are young and capable of much more than you may realize. Neither a college degree or investing in real estate will be easy. Life will throw you many curves over a lifetime, and you may need all of those options at some point. So why not do both?
