Cute, but ultimately kind of lacking and unsatisfying, Cherry Tree High Comedy Club (or CTHCC) is simultaneously too short, yet too padded out. The stat raising system and the exploration of the city is actually quite charming in its own way, but ultimately only serves to needlessly lengthen the play time of a visual novel that, quite frankly, doesn't have much to read in it. The story builds up, but ends where it feels like it's only getting started.
It never really managed to make me laugh; chuckle, at best, I'm afraid. Rather than think of it as a comedy, I'd more describe it as silly, light hearted slice of life... that said, in that regard, I've seen better media. Ultimately, though the writing and characters never especially moved me or captured my heart (they're a little bit generic, as if hodge podged together from familiar tropes and little else) I think that I'm only left with that impression because the game isn't long enough to give anyone a character arc of satisfying length.
Ultimately, it's kind of like playing a single month of Persona 3 or 4, minus the dungeon crawling JRPG side of things, but the fact that the stats never seem to matter for much and the scenes you unlock with characters never allows you to make any dialogue or action choices leaves the player feeling much more like an outsider to the experience. While that's fine for a visual novel, in this case it only contributed to the feeling that this VN was merely half done.
All that said, I realize there's a sequel, and, since I did get it in a bundle with the original, I may change my opinion after playing that. Both are fairly cheap, so if I think of them as a bundle it may end up worth it. Nevertheless, CTHCC2 has a lot to make up for, and it's going to have to tremendously exceed the quality of experience the first game gave me if there's any chance I'm going to turn around my opinion on the series.