Hong Kong used to be all kinds of cool. Not so much, now. I've travelled over 4 continents, though I've never been to the Americas .... In about 5 years or so I'm planning a motorcycle trip around the world. After then I'll feel qualified to give a definitve answer.
I always liked the Philippines, despite the danger and the violence. Singapore is pretty cool ... I couldn't live anywhere where it snows over half the year so that eliminates anything in the Arctic and Antarctic circles. Way too cold. Japan is .... ehhh? I don't know. I preferred Hong Kong, as the very city felt alive ... whereas Tokyo in the monsoon season is pretty horrible and bleak. Tokyo is *lovely* when it's sunny ... miserable when it rains. And the added problem of being 5'10'' in the monsoon season is you have to wear sunglasses just to protect your eyes to a wayward umbrella spoke.
I didn't mind Kyoto... with all its buses and horrible trains, it felt kind of like Sydney. Only less fun and with less gambling and prostitution. It straddled that line of defineably being busy, but still maintaining a measureable pace without frenetic motion. Nightlife is shit. Food is shit.... tourist attractions, while lovely (you can sit in... Ieyasu's(?) private water garden balcony) ... don't have that beautiful energy of naked consumerism you get elsewhere.
Which might strike people as odd for a student of history ... but I have far more respect for towers of gleaming commerce and consumerism over artificial solemnity and respect BECAUSE I'm a student of history and the past is largely a constructed lie based on simply wanting something other than what we have.
The past was shit. Remember why it was shit... make the future measurably less shit. So if you have a mindset like mine, Kyoto isn't the place for you ... plenty of places are promoted in a way that is; "Ohhh.... this place has history therefore value and demands respect." While I don't begrudge people who like things like that ... I can't get over the fact that any attachment is imaginary, and any *real* value lay in skeptical retrospection, not respect.
Ueno is probably the ... most homely? If all places I have lived in Japan. Nice mix of very quiet and very busy. Where giant highways loom over your head and little clusters of housing and business bathed in perpetual shadow live around and beneath.
Spain is a lot of fun and the architecture is *gorgeous*. I think Spain is probably the most liveable place in Europe if you already have money. There are few regions anywhere in the world that are as beautiful as the Costa Blanca. I have entertained the idea of buying a yacht and living on the water, and the Costa Blanca would be the place I'd spend 70% of my time.
If we're talking a toss up, I don't feel a desperate need to leave Australia and live anywhere else. After all, being trans I feel like Sydney is at least the safest place to live. That and we actaully have a working economy and the weather is just right in Sydney. Warm and dry. 90%+ fine or sunny days. And we have some awesome beaches.
But if I had to pick another place, I wouldn't mind staying in Alicante or Hong Kong again. Probably Alicante, as the native language would be easier to master.
