Having been a chiyuv myself, I think that the biggest challenges are minyan planning on travel days, and making sure your activity schedule doesn't take you away from Mincha - obviously this is harder in the winter than the summer. As an example - if you go to Disney in California, and are not guaranteed that there will be a minyan in the park, even if the nearest shul is 15-20 minutes away, it's still at least an hour away for you to leave the park, find your car, etc.
My two oddest stories as a Chiyuv:
- I was in a minor league baseball stadium with some friends - but we were only 7. We initially thought that we could make a late ma'ariv minyan, but were worried we wouldn't make it. This is in Florida, 30 min. North of WPB, and not in a very Jewish area. Then out of the corner of my eye, I saw one guy wearing a Yarmulka. He was there with his dad and BIL, just enough to make a minyan.
- My Dad's yahrzeit was the Friday of my Nephew's Bar Mitzvah. Normally NBD. Except I live in NY, and the Bar Mitzvah (which I was driving to) was in Detroit. I davened Maariv in Teaneck, Shachris in Cleveland, and Mincha in Detroit. Saying Kaddish in 3 different states over several hundred miles.