Rocco, you come across as someone who knows precisely what he wants. That clarity is praiseworthy, not a sign of douchebaggery.

One thing that never quite sat well with me in the digital nomad/expat community is how there is so much content geared towards "moving for the sake of movement." And while that might be fun for a while, I don't think it's sustainable. After several moves, or more insight about your likes and dislikes, one settles on a pretty narrow set of places and picks from this shortlist.