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Read the forum archives buddy. Answers to your question (whether you mean, sex, dating, or a monogamous relationship) are expounded on in length from the perspective of many expats in various parts of the world. It will be very much in your favor if you can maintain that income while you are traveling/re-locating (is it from online businesses?) or at least have an open door waiting to same job if and when you return. Read-up and good-luck.
I wasn't born in the U.S. and I can't figure it out as well. U.S. is totally screwed up with personal life. Girls are light-headed and don't even know what makes them happy or what the hell they even want in life. Again, if it was money, I would get it. Many girls in Europe just look for decent guy with money to support a family - I understand that (not talking about gold-diggers here), it is logical because there are many broke-ass guys. Now there lots of rich guys here in the U.S., but girls pick losers - white trash, hilly-billys, guys with drug and alcohol problems etc. That's total and complete madness!
If you want advice - what would you like to do? Do you consider relocation to Europe for a lifetime? I would say it would be the best thing you can ever do in your situation! Especially with your online income and money you will have from selling your truck - it will enough to get by in Europe, especially Eastern Europe. Italy is good too of course, but a bit more expensive compared to East. Also Eastern Europe will have the best looking girls with much fewer demands.
Oh yes, my friend just came from Russia. He showed me a picture of him dancing in the nightclub, he was THE ONLY GUY dancing there! Ratio in the club was 80% girls and 20% guys. But even those guys did not care about the girls, they were drinking beer at the bar and girls tried to hit on them all night, but guys just didn't care cuz there are so many girls around I wanted to CRY when I was listening his story!!!
I just moved to Europe and my Italian wife and son (both dual nationals, like you) are happier here. People are nicer and more genuine here, and having EU citizenship is ABSOLUTELY HUGE!! It gives you access to work, live, study, and get medical coverage in 27 countries. Most Americans have no idea the advantage having an EU passport is. Dude, you are so set for life. Don't' waste it. You can also pass both citizenships on to whatever children you have in the future, by cause of birth.
The Italian economy is doing better than the American one, despite what they say in the press. And some EU economies are just going fine, such as the Netherlands, Germany, Norway, Denmark, Estonia, etc. If you have a way to keep your income going, while living over here, you'll have much greater access to so many different cultures, cuisines, and women from different cultures. If Russia/Ukrainian women are your thing, there are more in Western Europe than in the US. In a nutshell, if you want to find a good woman who isn't ruined by the shallow American culture of entitlement, you will need to relocate yourself here. Get yourself a little apartment somewhere in Italy, get your internet business going, and go meet the ladies.