Let's think about this. Since the actual team you go to is not a consideration. Just the city.
Criteria:
1. Babes. How good, and how many you can get. Also, factor in how many other bigger celebs are around to compete with. LA and Miami are good. NYC too. But hockey hotbeds like Toronto and Montreal work well also because of your elevated status.
2. Other activities. Not just drugs. Nightlife. Accessibility of fun. NYC and LA, maybe Chicago top the list. Dallas?
3. Lifestyle. You want an idyllic surrounding for your babes and budding drug habit. A beachfront house maybe? Large mansion. can your money buy that mansion? Hot days, wild and crazy nights. Miami wins here. I imagine LA is more expensive. They say Vancouver is beautiful too, but they have winters.
4. Crime. Who wants to get mugged or murdered? No to DC and Detroit. Chicago maybe too. Glad Atlanta doesn't have a team anymore. NYC is not the safest place anymore either. Maybe Canada wins here? Or Minnesota/Buffalo?
4. Buddies. You're gonna have to bring your entourage with you. They ain't celebs, but they want legal recreational weed and affordable bars. So that's Canada again for the first, and maybe Denver. Home of Coors.
5. Media coverage. You want to be a star. But you don't want to be harrassed by lunat.... i mean fanatics. So scratch Raleigh, Columbus, Nashville, Sunrise where you don't get any coverage and you're a nobody. But also places you might feel weird and claustrophobic like Montreal and Toronto. Winnipeg? Edmonton. Heck, all of Canada.
What's the conclusion then? I don't know. All have their goods and bads. Maybe... St.Louis? The ultimate compromise. Nothing is too much like this or like that. Home of Budweiser.