I've previously enrolled in Apple's pay developer program, Select, as detailed at http://developer.apple.com/products/select.html . It provides access to releases versions of all standard (although not enterprise or protools) system software (effectively Mac OS X and Server) as well as beta access to all sorts of things, and a hardware discount voucher good for one computer purchase (although not an iPhone last I checked). The pay program also include some pre-paid code-level support incidents. Software is downloadable from fast server and major releases are mailed out on DVD along with monthly and quarterly update DVDs. This is $499 USD per annum and renewals are full price. With their release cycles renewal has never been worth it.
Microsoft TechNet Plus Direct
Microsoft's Tech Net Plus Direct subscription ( https://technet.microsoft.com/en-us/subscriptions/add/bb892756.aspx ) provides access to release versions and keys of standard system software, server tools, and office productivity applications and streamlined access to beta and RC-grade software. In their words, "Full-version evaluation software without time limits". It includes technical support incidents as well, although no hardware discount is included. Software is downloadable from fast download servers or can be mailed out for an additional fee ($599/449 renewal). This is $349 USD per annum and renewals are 249.
Keeping in mind that in all cases this software is only licensed for evaluation, doesn't it seem like Microsoft is offering a much better deal? If you actually had to license even the basic OS platforms just to evaluate, test, learn on them: Mac OS X Server (50 user) is $499 itself, Windows Server starts at $999 with five CALs and on the other side Mac OS X client is $149, and Vista (client) starts at $129 (Home Premium) / Ultimate $199. And I'm pretty sure MS is saying SQL Server, Office and other rather popular items are included, which could add up to another $5,000 USD that no one would ever spend for this. Apples full dev tool suite is a free download while Microsoft's costs money and is a much better array of tools. Still, food for thought.
And yes, all considerations of Windows operating systems are primarily for playing games, followed in priority by learning Windows Server, and then testing cross-platform code on Windows.
This started as a http://adric.livejournal.com/188710.html post on my lj. It began life as a very terse message to be addressed to Steve Jobs but quickly become something slightly more useful.