I think it's fine that you wanted to include some roles you'd like to have "just because" like the two Pirates, but maybe it would have been better if you hadn't put all of them at once in one single game
From your thoughts, I also think that the impression you have about certain roles is different from the one I've made for myself (which, for all intents and purposes, might very well be just me talking out of my ass), or didn't take into account - in my opinion, at least - the probability of those roles being used in one way instead of the other causing an imbalance in a setup which, like Gry said, is heavily based on randomness.
For instance, the few good targets for the Sane Apprentice and the Insane one, on the other hand, being more likely to be an asset to the town (at the very least, by confirming another townie) than joining the mafia, while the chances to become a second SK are much, much lower on paper. There was double the chance to see one of the two Apprentices learn from the Freeman than getting a second SK, for instance
What's more, an Apprentice can only start to be useful from N3, if they get lucky and target a good role from the beginning, don't get blocked by one of the two roleblockers, or have to start over because their first target died or became untrustworthy. That means they're not reliable ways to buff the town as a "jolly" role, but more of a "could be great, could be bad, but most likely will either be average or not manage to do much at all". The latter result being what happened for both of them in this game.
Then, some roles being included just to screw with the townies is also something that I think could have been toned down a little. Three Docs means one of them is almost certainly going to get lynched. With only one of them being reliable and another being completely useless (Naive doesn't even get fake results to share like meme Dets and Spies do, he just sits there thinking he's important), that's nerfing the already scarce protection that the town had, while it also meant having bogus targets for the Apprentices and Pirates, since they look good but are not.
On that note, it's also weird to see a Paranoid Spy in the game without a Sane one and with only two Dets as the other investigative roles for the town, while the mafia was given the Mafia Det to find and pick the roles to steal and kill - the poor SK included.
Other than that, the town didn't have any offensive or "trap" role that the mafia or SK would have to look out for - no bombs, BPs, PGOs, daykillers. Yet despite that, which I think was an interesting change, there were more townie roles that could kill others or themselves (which even happened in two cases, with the VT and the Hider) than roles that could protect (Doc and Hider, who ended up never saving anyone). In proportion, the ratio of useful power roles between town and mafia was tipped quite in favour of the latter as well.
In conclusion, I think the setup had some nice ideas, but just too many incompatible ones being stuffed into the same game made it a bit of a mess to play. Or that's the impression I got from playing half of it and spectating the rest. A lot of unpredictability stemming from several elements (two Apprentices + two Pirates, three Docs, Insane Doc, meme Spy, Freeman, SK) means it's harder for townies to formulate strategies and follow a sensible plan, but that's never actually been a thing so you can disregard this point
But seriously, it makes the game more relying on going with the flow and the town mainly having to avoid the pitfalls from the unreliable townie roles themselves rather than chasing the scum. In fact, I'm almost sure that losing all the result-producing roles and not getting them learned or stolen in the process was instrumental to the town's victory
And I know I addressed only
@Emperor Spriggan in this, but don't think I don't know who else is actually responsible for some questionable choices here