Also, it seems the same graphics engine was further used (and refined?) in baseball games - with the Hardball series. These, of course, had little traction in Europe. How was it in baseball friendly geographies? How did the popularity of the baseball games compare to the Olympics titles?

Very condensed tl;dr: winter games had a DRM that makes the game perform poorly if you enter wrong code; most of the cracks (including an "official" crack from 1996) skip it wrong and therefore you have a broken game; that includes gog.com version.

This person actually released a "patch" for gog.com version of the game.

https://mrwint.github.io/winter/patcher/index.html

Was a big fan of the summer one though. I could get gold medal in every discipline on highest difficulty level except for the horse. I could never figure out the horse one. I think I managed to beat it only once, ever.

Ski jumping was fun, too, and I think I was a horrible shooter in biathlon. Fond memories on a 25MHz 386SX (and of all those other pirated games, in the early Post-Soviet Eastern Europe) for sure!