I can't read Crosby's mind but for the sake of this post I'll add my 2 cents.
If I were Crosby I would have 6 choices:
1- Favorite Team: Crosby's fav team is Montreal, therefore he would pick them since it would be his dream to play for his fav team, for example if I was as good as Crosby and I had a choice to pick any team to play for it would be the Wings since they're my fav team and it would be a dream to wear the jersey of my fav team.
2- Money: We're all humans and sometimes we want more money, if Crosby is after the most money then I can see him playing for NYR, Detroit, Toronto, Philly, or any other team that offers the most money.
3- Future Powerhouse: If Crosby wants to win future Stanley Cups and rack up big numbers then I can see him picking a team with loaded young talent, good examples would be Atlanta and Florida since they have a bright future.
4- Spotlight: If Crosby thinks he could help a franchise and put his name in history then I can see him joining a team that's struggling just so that he can save them and earn the spotlight, of course good examples would be the Rangers, Buffalo, and similar teams.
5- Near Home: There's always a chance that Crosby want's to play somwhere near home and be close to his family, if that's the case then I can see Montreal, Ottawa, or another team close by.
6- Favorite Area: We all have fav areas we like to live in, for example I like hot places and my dream is to one day move to Cali, Crosby could have a fav spot that he wants to live in, if that's the case then it could be any team depending on his fav spot.
Having said all that, we don't even have a CBA set, so until then this is all moo talk.