Eye-watering perhaps, but not unreasonably for what you got. Although the top-tier Enterprise editions truly were eye-wateringly expensive, and provided nothing compellingly useful that wasn't available in entry-level or mid-tier MSDN subscriptions.
My preference was for a mid-tier subscription that provided a complete set of licensed-for-development-use Windows Server, and Microsoft Office and SQL Server ISOs, for ~$495/year.
Of course, you had no way of knowing that the truly eye-watering top-tier $2000/yr MSDN subscriptions were jam-packed with junky "Enterprise" tools that you would never actually want or need, without actually purchasing one. Nor would you know that the priority support credits bundled with top-tier MSDN support did not materially improve upon the "shouting into the void" nature of unpaid support, which in turn was not materially better than the No Support At All for U option that we currently have. Although my one experience with a paid priority support case did actually produce an actual fix three years later. So there is that, I suppose. :-/
If I recall, MSDN was super expensive but that is because it included non-commercial licenses for just about everything Microsoft shipped as well as getting hard copies of the documentation and a bunch of other stuff.
If you just wanted to do c++ windows programming you can get visual studio which, I believe, did come with Win32 documentation (especially as CD roms became common distro methods).
The c++ software development kit itself (just libraries, documentation, and samples, no tooling) wasn't too expensive and was mainly material costs.
I always drool over those paper documents. Imagining myself getting into some underground facility due to WW3 and hacking on some old computers reading those manuals is one of my comforts.
