7 cities, 3 countries (US, Taiwan, Canada). Did NYC twice actually, about 8 years apart.
Adjustment strategy varies. If I am the prime mover, it's easier -- I am moving towards something, maybe have a job or academic program to plug into. It's nice to have friends and family nearby, too.
It's harder if I am the trailing spouse, as has been the case a couple of times. My most recent move has been the hardest ever in terms of adapting, so I can't say I have a bunch of wisdom to share at this time. You'd think I would be a pro by now, but every move is different.
2014 Bobbin Bramble / Brooks B67
2008 Rodriguez Rainier Mirage / Terry Butterfly Tri Gel
2007 Dahon Speed Pro TT / Biologic Velvet