Did individual developers actually pay that? I’ve done quite a bit of development in the MS ecosystem and can’t recall anyone personally paying for MSDN. It was always through their employer that they got access.
Individual developers paying was always an insignificant volume. It was still within reach so devs could get it and be productive. As an example, the cost was fairly insignificant to the many .NET devs who jumped to SharePoint in the 2000s to keep their top rates. People give SP a hard time quite rightly, but as a revenue generator for devs in many markets with limited options, it was a very good choice.
It was priced and designed for companies to be buying as a bundle with other licensing. individual devs would frequently use some of the loopholes through licensing partners to commit to what was basically a three year subscription that spread the cost. For companies, it could mitigate some of the costs associated with the proliferation of environments that needed to be licensed from top-to-bottom. Later, these may stop being eligible for MSDN use and generate more revenue. License auditing was real and gave visibility into this usage.
VMware still have a program like this going for their admin user base. It gets recommended by the r/homelab folks who haven't adopted Proxmox.
I definitely had some sort of personal MSDN subscription at one point. Plus compilers and the tike were far from free. I had shelves of books. And computers themselves cost more in inflation-adjusted dollars.
