What finally got you out of your home country? And how did you decide where you were going? I’ve never even left America, but being a digital nomad seem so interesting. I’ve been looking into it for months, but any time an opportunity comes to actually start doing it, I panic. I keep letting little things get in my way, or little fears stop me from actually making any changes. Should I do some traveling before just leaving or should I get out before I lose my nerve?
I met my girlfriend 
You can definitely go to EU for 3 months (as much as you’re most likely allowed, without having to register your residency or have visa), then do the same with countries that are in Europe, but not EU (e.g. Serbia), then back into EU, or try Turkey…
That will give you plenty of time to figure out if the lifestyle is for you, if you miss the US that much etc. 
That sounds like a great way to do it. Bold yet a little bit noncommittal at the same time. Is that what you did? What did you do with your stuff back home (I mean big stuff like your car).
I haven’t yet gone ‘full nomad’, but when my husband and I were looking into graduate programs, we checked out some in the United Kingdom (from the United States). I didn’t think moving abroad for a graduate program would make sense but somehow it did! It’s not a good path to citizenship, and it’s a bit different from the total lifestyle change of being a nomad, but in a lot of ways it was a less scary step. Now I’m in love with living abroad and want to try a location independent lifestyle!
If you’re interested in a master’s degree at all maybe check it out? It’s hard to learn in a totally different system, but it works for some! Also, a lot of european master’s are only a year and much more flexible than American ones. Lots of time to travel.
My circumstances made me move into a neighboring county, so I moved most of my stuff in 2-3 car runs and the rest left at my place in my home county.
If I were you I would make a power of attorney on family member’s name and leave a car with them. If you decide to come back, it’s waiting for you. If not, the family can sell it and wire you the money.
All the other stuff can be sold, given away or left with your family.