Yes, I see what you mean. If you've had an article published in print that hasn't appeared online yet, that does make things more difficult. I think you're right that it would be better to write different articles for print and Medium.

Yes, people do seem to like to read about personal experiences. But only if they are interesting, entertaining, or informative. The types of personal articles to avoid are the ones that would otherwise just go in a private journal. They are not interesting to anyone else. Nobody needs to know the normal day-to-day ins-and-outs of whatever's going on in our lives. It's the ABNORMAL stuff that's worth writing about.