We visited CC twice, so I can answer some of your questions with regard to this school. It is best known for the block plan - one class at a time 3 hrs a day, with a 4 day break in between. Kids study every day during the block bc they have to be ready for the next day. We were told to think 8-8-8 (class/studies, everything else, sleep). The school has an alternative and outdoorsy vibe, and is very accepting of all types of people. Fabulous access to outdoor recreation and skis, etc, are rented for a pittance. Pot/weed is prevalent. Frats/sororities non-exclusive (not a big influence). Not preppy. Getting better with career services, but many go to americorps, etc. before grad school (major dependent). One concern was brought up by pre-meds (if applicable) that it was difficult to get their required pre-reqs in 4 yrs due the way blocks are picked. Liberal school in conservative Colorado Springs. Very pretty.
Good friend’s son was at Whitman. It’s not as left as CC, but still liberal and not preppy. Most kids love it, but he left bc he was very introverted and missed home. And, it’s kind of remote.