I'd strike Portland and Baltimore off of that list and replace them maybe with Seattle and D.C.?

The greater Portland area ain't bad, but downtown Portland kind of blows. The food scene is okay, but it's hard to get just normal good greasy spoon food without having to find out more than you want to know about the meal. Seattle is nicer is almost every way and has more to do and a far better tech scene.

Baltimore is a hell hole and I wouldn't miss it if it sunk into the ocean tomorrow. I grew up not far from it and avoid it like the plague. It's one of the saddest U.S. cities outside of Detroit. I'd say the same about D.C., but it's improved tremendously in the last 20 years and is actually not a bad city these days. It's not as nice as modern NYC, but it's getting there.

Having done lots of global travel, including to Australia. I'd say the bits of Australia that I've been to (NSW) were "fine". It feels very "American" in lots of ways, but different -- like an episode of Sliders. Public transportation was even worse than the lousy standards of the U.S., if that's believable, and everything from real estate to food was terribly overpriced. But it had a nice feel to the place, people were friendly enough and there's a better fitness culture than in the States if that's important -- it's not to me. The big spaces between the cities were full of the same kind of redneck you find in the big spaces between cities anywhere and only appeal to people who like farming and dust. As an American I could see moving to Australia for a couple years maybe.

Europe has nice bits and "meh" parts as well...even in Western Europe. Growing up in one of the most cultural diverse places in the world, the lack of cultural variety in lots of areas in continental Europe is kind of boring. Unless you count Kebabs and Chinese takeout as culture. London can service this if you need but it's about the only really strongly diverse multi-cultural city in Europe that's on the scale of the typical American city. The racial segregation in most of Europe makes Chicago look like a well integrated city. Europe offers good health insurance, and excellent local food (even if the variety isn't very good). But you also get high taxes, a difficult labor environment and in general an anti-risk anti-entrepreneurial environment.

The Middle East is well...it is what it is. A couple nice cities in a very difficult socio-economic environment with one industry. Depending on how you count it (European or Central Asia), lots of Turkey is actually pretty nice.

I count Russia as its own thing. Cities are pretty new like Asia, industry is highly focused like the Middle East, people can be very friendly once you get to know them, and then everybody's miserable anyways.

TBH These days I'd rather live in one of the newer Asian mega cities: Tokyo, Seoul, Beijing, Hong Kong, Singapore etc. Nicer places to live, better quality of life, more to do, and everything's newer so it's in better shape. Public transport is out of this world, and food is generally plentiful and cheap. People are fine as well in most places. Crime is also low and medical care is stupid cheap even if it's not universal. Most of Asia is also highly entrepreneurial with nearly everybody trying to start a business of some sort.

U.S. is big, varied, cities are generally metropolitan, lots of different industries to work in. The countryside drops down the socio-economic ladder very quickly. Pockets of extreme religiosity can be annoying but are easy to avoid. But it's medium-high entrepreneurial tendencies and high risk acceptance and well regulated banking system make doing business reasonably pain free. Health care costs are absurd, sometimes even with insurance. Food is of a high variety, even if much of it is second rate. Local American cuisine is generally contemptible, but pockets of traditional american greatness exist in the food world. Clothes and goods are cheap and plentiful and of unimaginable variety. In most of the country real estate prices vary considerably within short distances. Public transport outside of a few cities is almost third world.