Lots of great ideas already given; here are my Top 10, based on sex and gay community
1. San Francisco - Beautiful city, great community, sex; cool crisp, mild weather (not too hot, not too cold)
2. New York - Big, bustling, broadway, bareback; As long as good with the cold winters
3. Chicago - Fun, slutty city - big leather community, bars, gay neighborhood, and its cold
4. Ft. Lauderdale - if you want a gay city with sex in a warmer climate
5. Provincetown - Most densely gay populated in the summer; quiet in the winter - yea and I'm here now
6. LA/WeHo - California, but warmer than SF; good opportunities
7. Palm Springs - Even warmer than LA, and closeby (counterseasonal to Provincetown)
8. Washington - People forget out our Capital as a great gay friendly city / close to other east coast points too
9. Seattle - Often also forgotten about - a young city with vibrant gay life - a bit less expensive than some
10. San Diego - Warm city, great community
If you consider north of the border:
- Montreal, Toronto, Vancouver are awesome cities
If you want some other cities that are not always thought of first, but have great opportunities:
-Denver, Columbus, Philadelphia, Miami, New Orleans