I wish I'd had my uke:
1) While my father-in-law was still alive (He was BIG into music and loved the songs of the Roaring 20's, Al Jolson, and the WWII era)
2) While my mother-in-law and grandmother were both in the same nursing home at the same time. We had a small group of residents who used to meet in the lobby several nights a week at 6pm and I would play old recordings on my computer while we all talked and goofed around. It was a very special time for all of us, but it would have been really amazing had I taken up the uke around that time.
This Christmas, I brought my uke to my mother's house in Florida again, although it never seems to get played while I'm there. I almost left it home this time, but I grabbed it at the last minute. For the first time ever, not only did it get played, but it contributed to one of the best memories my mom (and her best friend) will have. I had brought some sheets of Christmas songs and we sang our hearts out to each and every one of them. Unfortunately, I forgot to bring my Old Time Singalong book, but I was able to fake my way through songs like "Ain't She Sweet," "Yes Sir, That's My Baby," etc, so we really had a great time.
From now on, the uke comes with me EVERYWHERE!
(This was a great idea for a thread, by the way. Thanks, ukunuke!)