I worked for a large manufacturing / consumer product company as a .NET developer and the four people on my team all had top level MSDN subscriptions. ( http://msdn.microsoft.com/en-us/subscriptions/buy.aspx )

I think the number I heard for our team, just MSDN subscriptions, was around $25000 a year.

That's only like 35 copies of Photoshop. Not to downplay the money you spent, but the market for Visual Studio is smaller than Photoshop. Also, the customer of Visual Studio is team leads and management, not actual users. This might explain why more expensive VS packages emphasize collaboration and team features.

VS.NET is something of a special case, since Microsoft would like nothing more than to give it away for free. They don't, because if they did it would make toolmakers like ReSharper and CodeSmith seem unjustifiably expensive.

If you're a small shop, you can get in thru BizSpark and get a pack of MSDN licenses big enough for your whole team for something like $400, all in.

So sure, you can pay $2500/copy retail if you're big enough to do so. Or if you're small, you can pay peanuts. Say what you want about Microsoft, but they go out of their way to take care of their developers.

Another great reason why selling a premium IDE is difficult.