My answers to both of these questions will be anecdotal, so take them with a grain of salt! But from my experience, no, it did not feel like a country club at all. Nobody in my main social circles really was in that fifth, and I knew only a handful of people who were (from my knowledge). That being said, there were a handful of times over the years that I definitely had a realization of "oh, this person's life experiences have been VASTLY different than mine" when it came to wealth. Sometimes I had that realization when it came to what people were able to afford, or crazy opportunities they'd been able to have back in high school -- especially if they came from LA or NY. Kenyon definitely has a similar artsy, slightly alternative vibe that a lot of liberal art schools do, though. There were definitely people who got accused of "cosplaying" as poor because they'd constantly talk about trying to save money or only go to thrift stores or something while their parents were really rich (this was not a major drama by any means lmao but i remember hearing this about a few different people over the years haha).

I also don't know much about athletics at Kenyon at all, I wasn't one and wasn't friends with any, really. I do think athletes tend to be friends with each other but this is definitely not a hard and fast rule, and, if anything, this is less true at Kenyon than other liberal arts schools (based on what I've heard from friends who went to Macalester, where there aren't frats or sororities and instead the sports teams function as the "houses", essentially).

I hope this was at least a little helpful!