As long as the Yanks have money, they won't have to worry about prospects. They just buy these players like none other. The Yanks do surprisingly draft well. The Yanks were the team that drafted Damaso Marte. Pettitte, Jeter, Posada, Bernie, Rivera, etc. came from their farm teams. Actually a lot of the Yankees success in the 90's came from their farm teams. I know the Yanks haven't won a WS since George has gone insane and started to really spend the green; however, you can't say you would have a better shot w/ any other team.
I just don't understand how you can become a "true" fan of that team, when you have a totally different roster every season. They're basically rooting for laundry in NY. I'd love to win a WS any way possible; however, I think it would be much more gratifying to win it w/ players from your farm and what not.