Nobody has dunked on Trails in the Sky yet, is this a good one to roll with?
The Trails series is one of my favorites, but it has high highs and low lows and you have to go in with tempered expectations.
The two starting points I would recommend are Trails in the Sky FC, or Trails of Cold Steel 1. Whichever appeals to you the most.
Trails in the Sky is a 50 hour long game, but the first 20-25 hours are boring. The story begins to become interesting towards the end of chapter 2/at the start of chapter 3 when you go to Zeiss. From then I became really enthralled by the plot. Unfortunately the game doesn't have that much going for it outside of the second half of its story. You're traveling through boring forests and rocky mountain paths and samey looking towns. The combat and character building isn't very fun, and the sidequests are mediocre. Fortunately they have since patched in a turbo-mode since I played it, so you can just hold down a button and fast forward through all of that boring stuff and get to the good part quicker. The game ends on a cliffhanger which continues into Trails in the Sky SC, which I didn't find as enjoyable (gameplay is the same, setting is the same, plot is 60 hours but the first 40 hours are pretty boring as you chase villains around accomplishing nothing while the B-team is off actually progressing the plot offscreen). Not bad, though. The 3rd Sky game was pretty fun, both in the story and in the combat and character building.
Trails of Cold Steel I absolutely loved. The game is 90 hours long but it felt well paced unlike the Sky games. I was never really bored. It hooked my interest from the start. You get to visit a lot more places, and I found them to be a lot more interesting both visually and lore wise. The combat and character building is also fun. The sidequests are also okay. Great music too. The second Cold Steel game is also fantastic, and avoids the usual pitfalls that plague Trails sequels. Trails sequels are usually about frutilessly chasing murderous psychopaths around only for them to escape scott free, but CS2 has you fighting a civil war against your own countrymen, who are moral people (and the Ouroboros characters who do show up are presented as cool frenemies), so it doesn't feel bad when people aren't caught and punished. CS2 also had one of the best endings in JRPGs. The first two Cold Steel games also had a very good English voice dub.
The Crossbell games and the latter Cold Steel games (3 and 4) have pretty
rage inducing writing (the gaslighting, the apologism, the heroes becoming traitors to their own countries, etc, actually these issues were present in Sky but it's pronounced here), and also have horrendous pacing issues. That being said, I did at least enjoy them enough to finish them, though I probably wouldn't ever replay Crossbell or recommend it. I did not like that it was set in a boring urban city, didn't really like the cast, and for despite having been made after Sky the 3rd (which had great combat), the combat and character building felt meh like the first two Sky games again. The latter Cold Steel games threw away the interesting plot direction set up by CS2's ending, but still had a very likeable cast, an interesting setting, great music, and really fun combat and character building which kept me thirsting for more even as I laughed at the writing.
The Trails games on PC have top quality PC ports, ports that all other PC ports should aspire to. Props to Durante.