Earlier quoted context omitted.
As a former American who lived abroad for about 11 years before renouncing, “cartoonishly cruel” is a pretty accurate description of the system. It’s even worse an American entrepreneur abroad because that makes things even more complicated. I gave up jumping through the hoops in 2018 and the self-torture and renounced. I shared my story in case anyone is interested: https://larrysalibra.com/goodbye-usa/
Have you ever wondered if it weren't HK - where your exit country would be? Did Italy or any other place in the EU appeal to you at all? I hold dual US-UK, which means the EU isn't really an option for me anymore.
I’ve certainly liked visiting a number of places in the EU - it might be fun to try to live there.