Now this is a good question. Can't trace any light-bulb moment.
I was once a member of a camera club, when everything was darkroom-generated and almost everything was black and white 35mm-based. I bought an MPP camera and got hold of a monster of a 7x5 MPP enlarger that needed rebuilding. When I moved to a much smaller house, (life is never smooth) all I could make were contact prints, but I don't think this was a major factor in changing over, although I did find the size restricting. In retrospect, it was a very good exercise – there's no hiding place in contacts.
I believe the changeover began when my employer began to use computers and I had to learn quickly. This was in the days of QuarkXpress, but we used Photoshop of course. I remember being astonished when someone demonstrated how to clone a flower and place it somewhere else. I became familiar with Photoshop and Illustrator. I still like Illustrator although I have high hopes of Affinity.
All this time I was still making darkroom prints but when employment retired from me, I was able to take my now-outdated Mac with me. We moved again, and I had a darkroom. At this time, the advantage in monochrome printing lay clearly with the wet process, but my digital colour prints were better than my darkroom ones. I was at best an adequate colour printer, perhaps because I didn't do it often enough.
It began to seem to me that I had much more control on screen than on-easel and I quite liked the micro-tinkering.
As printing technology improved, I began to process my negatives for the scanner rather than the enlarger (basically, less contrast, as you know) and now I seem to be using film originals in large format with digital output on a nice Epson printer.
Although I do possess a couple of digital cameras, I've avoided getting a clunky, clumsy, heavy and over-complicated DSLR. At the moment, I seem to be perched between LF and my iPhone. I haven't joined an iPhone forum, if there is one.
For me, the major disadvantage of digital production is the wide variety of back-aches that it provides.
I'm not sure if this properly answers your question, but now you've induced me to think of it, I don't think there is a single answer. A succession of circumstances, perhaps, with a bit of curiosity thrown in.