I really don't know what to think here, because the episode started slow paced and self-indulgent, and had some of the best scenes of the series to date by the end.
I'll start with the bad, because most of the bad was at the beginning. The episode was completely ill-conceived on a base level. First, the inclusion of Tilly was random, almost feeling like they felt they had to have her appear once, so they chose this episode. What's particularly jarring here is that Tilly is now a drama teacher - something which in no way comports with the (thin) resume we know about her after five years of Discovery. This is a new Tilly, because it's not really Tilly, it's Mary Wiseman, teaching kids about the healing power of theatre, something that Wiseman (as a thespian) obviously cares about.
The whole play scenario is also just ill conceived. First, it kind of stretches credulity because Starfleet Academy is supposed to be space college, not space high school, and you don't have gen-ed requirements in the fine arts by that age. Though admittedly, considering how much community theatre was on TNG, maybe there's just so much down time that this stuff is considered more essential in the future. But the bigger issue is that most viewers (myself included) know nothing about Our Town, meaning the metaphor this episode is meant to hinge on will fall flat for most of the audience. This is is the writers writing for the industry - for writers and actors - waxing poetic about the depth and healing power of drama. This whole side of the episode probably seemed brilliant to them, but flies over our heads.
Thankfully, that's only half of the episode, and we're quickly introduced to the SAM/Doctor sideplot (with Ake coming along because Holly Hunter is the lead, and needs something to do). Picardo is acting his heart out here, and given weighty material. Kerrice Brooks is great in the one scene where she's in the shuttlecraft and talking around her fear of death as well. There's things I don't like about the setup of the Doctor's trauma (really, he's lived for 900 years, and the one pain he's been holding onto forever is his holo-child? Torres was apparently the biggest monster in history), but Picardo sells it so utterly I don't give a shit. This stuff is all great - no notes.
Turning back to the other side, I guess we have to talk more about Tarima, since she's the character who goes on an arc here. Unfortunately, even though she lands somewhere better, I was left by the end of this episode from having shifted from indifference to active dislike. It might be Zoe Steiner's performance (which I continue to find lackluster) but I'm really sick of her "not like the other girls" bullshit, and just wish that Caleb would wise up and date Genesis instead. Obviously everyone is deserving of love, etc. etc., but she's very much in a "needs to figure her shit out" portion of her life, and everyone should stay far, far away from her in a romantic sense.
Oh, and I guess last week's episode was completely unnecessary? The only possible thing from it that actually mattered was the few minutes of romantic tension between Caleb and Genesis, which Tarima wasn't even there to see, and so she shouldn't have a reason for jealousy. Besides that, we could've skipped ahead and nothing would have been lost at all.
So yeah, hard to rate because the first 20 minutes or so were really, really bad, and then it won me over in spite of myself as better and better scenes came to the fore. There's some great character work mixed in here. Too bad it's not attached to a better plot.