If I am remembering correctly, this was also a good time to be in Linux. Since the Linux world operated on source code rather than binary blobs, it was easier to convert software to run 64-bit native. Non-trivial in an age of C, but still much easier than the commercial world. I had a much more native 64-bit system running a couple of years before it was practical in the Windows world.

Linux for Alpha probably deserves some credit for getting everything 64-bit-ready years before x86-64 came out.

It also helps that linux had a much better 32-bit compatibility than windows did. Not sure why but it probably has something to do with legacy support windows shed moving to 64-bits.