Yeah, that's quite the question. The forthcoming release of Visual Studio 2005 and SQL Server 2005 brings with it a change in the MSDN subscription program.
Right now you can get a Universal subscription for about $2,400 which more or less will get you everything that Microsoft currently makes. When the new version is out, there are essentially two higher levels above Universal (which will be called Visual Studio Professional Premium or some such nonsense). The next highest level includes one of the Team System skus, either for architects, developers or testers, because some moron at Microsoft seems to think that these are actually discreet roles in every organization. That'll cost around $5,500. If you want all three versions, plus the Team System server product, that'll cost you more than $10k. No thanks.
I do want Windows Vista and Office 12 when they come out, but the truth is that I can get that with the Pro-Premium version when it comes out. They're saying $2,500, but I suspect it will be less at retail. The Team System tools aren't worth it all split up like that, so they won't get my money for that. If I buy the Universal subscription today, I get upgraded to one of the $5,500 versions at no cost, so I guess I might as well.
Microsoft has really taken one step forward and two steps back this time around, and it's annoying. They're making the cost of entry into their platform inexpensive even for the hobbyists with sub-$100 development environments (the Express line), yet they're pricing the good tools ridiculously high, and fragmenting the features all over the place. Stupid. On one hand they see the money in selling server licenses so they'll get you in cheap, but then bend you over if you really want to get the most from the platform. I still say that the cost of software isn't a big deal compared to the cost of labor, but they still don't get that independent developers like me are the ones pushing clients to use Microsoft in the first place. It makes our jobs that much harder when open-sores people are screaming "free! free! free!" to the same people I'm trying to sell.
I bought a subscription shortly after being laid-off back in 2001, and it changed my life. This time around, I'm not so sure I need to take that leap, because now I know how to be profitable, and the only thing I need (as opposed to want) is Visual Studio.