I went through something similar near the end of life of Windows 95. When most of my data was in Microsoft Office. So I managed to get it online by switching to Google. For anything that I couldn't get online, I briefly used Linux Mint. Briefly being a few years.
Long before I retired last year, I had everything online. So that I could work anywhere in the world without interruption. My office was wherever I sat with my Chromebook.
I think that the online move is easier nowadays. Around 3 years ago I had a similar chat with a photographer. "Not possible," he said, "because I have too much raw photo data to move it all online and I need [name of Windows apps forgotten]."
Earlier this year, as we were chatting about imaging software, he revealed that he had moved to Adobe Cloud.
!BBH