Whoa. That's a lot to reply to.
My opinions only:
Europeans are in many ways culturally ahead of the US. As I've told my wife, whose maternal side is from English Puritans settlers, when those Puritans left England and established colonies here, that lloosened up England and the US got tight.
Many of the crappy regulations in the EU were imposed by the EU bureaucrats in Brussels without countries/people voting on it. That's the sad nature of the EU. (And, though born and bred in the US, I have dual citizenship, so I feel quite bad about it all everywhere.)
Weather: I lived in England for two years and I liked the weather there. (One year in Oxford and one in London.) It rarely got too hot. And, the usual portrayal as raining all the time doesn't really apply to the east coast of England, in my experience. (Though it certainly does on the west coast, where I spent a couple of months in cold rainy dreariness. Though beautiful too.)
Often, by the time the weather pattern moved east, it shed its rain.
Italy is like the US. One can't generalize about conditions. When I mentioned broken infrastructure I was only talking about Rome, which I love dearly. Other big cities there are better. In Rome, there's garbage in the streets because the trash pickup is so inefficient, the mass transit can be seriously screwed up.
And last, funny that our opinions about NYC should be totally opposite. I used to really dislike NYC (and that's where I was born and raised), but despite the larger population, it's cleaner and safer and friendlier than it used to be.