Those Crossbell games and the Cold Steel games are in an awkward place where they spoil each other.
Maybe I'll make a full topic on this after I've played Trails to Azure. CS1 and CS2 are much easier to play and I wasn't incentivized to push through the slog of early Sky until I felt I had to in order to keep playing the series. I just don't think it's a good place to start. Especially if you have the voice packs patched in, you can hear all the emotions swirling around in Estelle's voice at the end. The conclusion to Sky 1 is the best out of all these games. Once the metaphorical and near-literal training wheels come off by chapter 2, the game picks up pace and once the plot kicks into full gear by chapter 3 and the finale and all the shit really hits the fan, the game's quite good. Like, sometimes he's a little cute but usually it's too much. At his best he's an innocuous player in the Zemurian political game, but often he's as obnoxious as the characters in-game say he is. Also, while I love Estelle and Joshua to death, I cannot understand the love the community holds for Olivier. The whole affair makes Scherazard look awful at her job. Not as much leeway at the end of chapter 1 where they do it again, only this time in the confines of an underground shelter, the only escape from which involved running around your team to the door. The thieves you're pursuing escape via a smoke bomb in the Prologue, although some leeway can be given because they use an airship to do so. And the chapter conclusions are really bad. The game doesn't give me a reason to keep playing through its basic-ass combat and basic (literal) trails. There's payoffs to all this stuff and it's all developed well but none of it is enticing on its own at the start (despite really liking the actual individual lines of near-everything). You bite off a bit more than you can chew on your starting quests and get saved by your superdad. You meet an unassuming archaeologist inside who has a character portrait for some reason. boring to listen to (although that might just be me), and the usual fare of introductions in Trails games is at its worst here: You explore a giant, mysterious tower near your town for a news duo, including an at-the-end-of-his-wits journalist and his enthuastic but witless photographer.
Combat starts kneecapped with very little to do and the AOEs you get are narrow to the point of 'might as well be single target'. This is what I'm doing now and I'm just waiting for Geofront to release an enhanced edition of Azure so I can finally play CS3. Ideally, CS1 & 2 -> All 3 Sky games -> Both Crossbell games -> CS3, etc. As someone who tried and failed (and know two other people who tried and failed) to start from Trails in the Sky 1, I recommend starting from Trails in Cold Steel now. This is a really popular position but I can't say I agree.