This is a very good question, and I have come to realise that only by living somewhere do you get to see it warts and all.
I lived in Cyprus 2005-2010, and you can get fed up and bored with antiquities, sea, sand, sun and cold beer. (Working on a building site in temperatures of 40/100 + for €25 a day isn't much fun, either).
I am happy with where I live in the UK - a mainly rural county with a beautiful coastline, and I have family here. But I love mainland Europe - the freedom to put the car on a ferry, drive off and turn right for Spain/Portugal, straight on for France, Germany, etc. (I confess to making up 'dream' journeys on my satnav.)
I've only been to the US once, on a case, and spent three weeks there (mostly rural Wisconsin). I liked Madison, WI, (there's reality then there's Madison) and even had a half-formed plan to move there and teach at UW. Didn't come to fruition and probably for the best. IMHO the US can be good if you are youngish, have a good job with medical insurance, and so on.
I once had the chance to go for a secondment job based in Miami as part of a joint FBI team covering the Caribbean. A dream job, perhaps, but the security information about the provided housing for me and my family was rather off-putting.
Like so many things in life, I think, you need enough money to give you choices. Living on an island (e.g. CY) is fine if you can afford to fly out as and when you wish. Living in a country with no NHS is fine if you can afford medical insurance or the bills as they arise. And, if you have family ties it's good to live within reasonable/affordable distance.
I still don't know where I will end up.