Hotchkiss parent here, happy to answer questions. And congratulations!
Because there is a big number of incoming 10th graders (“lower-mids”), I think they find it quite easy to integrate. Usually there are 40-45 new lower-mids, so you’ll have plenty of company in figuring out how everything works. And the orientation program before classes start seems to be a big help in everyone getting to know each other. I think that after a very short period of time, no one even remembers who started as a prep and who started as a lower mid.
As for workload, it definitely ratchets up each year. But you also get more adept at managing your schedule each year. I think of it as being akin to the saying “God doesn’t give you more challenges than you can handle.” I’d say that most kids are pretty good about using their free periods during the day to get some work done, which makes a big difference.
As for weekends, most kids really like that Hotchkiss is somewhat isolated, because it means that most kids stay on campus, so there’s always a lot going on. Saturdays are always busy, because most Saturdays there are classes, and then sports take up the afternoon. Saturday night there’s almost always some event – a dance, a magician, movies, etc. Sunday is quieter, most kids sleep in, each brunch late, hang out with friends and get some homework done. The school runs buses into the nearby town of Millerton so you can go to CVS, the grocery store, and the local coffee shop (which is awesome!). In nice weather, kids will also go for a walk in the woods, sun themselves down at the lakefront, or maybe do some extra workouts for whatever sport they do.
Saturday classes, on the whole, are looked at as being a plus. Yes, there are times that everyone wishes they didn’t have to get up for class on Saturday. But the counterbalance to that is that your classes are more spread out over the course of the week, so you have more free periods during the week than you’d otherwise have, and your homework is spread out over 6 nights instead of 5. Plus typically it means that you’ll have some other day of the week that isn’t a very hard day, so the night before that is a nice little break mid-week.
Your actual transcripts (like for external use) just shows your final grade in the class (so if it was a year long class, it’s for the whole year). Internally (and for parents) what you see is a grade for each marking period, the exam, the semester, and then the final (if it’s not a semester long course). Plus twice a year, the teachers write very detailed comments.
Hope this all helps!