Honestly, why has no one brought the fact that Falcom is litteraly remaking the first game in the Trails franchise ?
Trails in the Sky should and will be the game to recommend to new people willing to experience the franchise.

I mean, personally, that'll be my first Trails game anyway because there's no way I'm jumping in the middle of an arching story while barely understanding it's world.

Nice. But I'll wait for them to finish a remake trilogy and then jump on. I'm not buying in on a promise. 

Unicorn Overlord.

If you want to play Trails series, wait for Trails in the Sky 1st remake.

If you dont want to wait for the remake - buy the Trails in the Sky series on Steam (where you can at least do mods to speed up the gameplay). Warning though, heavy text game and slow gameplay/battle style.

I've only finished the first one but I'm gonna do a second playthrough and eventually play 2 and 3 back to back.

As crazy as that may sound - nothing can be worse than the Legend of Heroes Gagharv trilogy on PSP - its slower than The Legend of Heroes Trails in the Sky trilogy and the translation was horrendous - I clocked over 160 hours between the three PSP games lol.

Wai what ?! It's the first I've known of the Gagharv trilogy lol. I always heard of people going from Sky's to Zero/Azure instead.

Technically Sky First Chapter is the sixth game.

The reason why people go from Sky to Zero/Azure is because they are all under the "Trails" sub-series of The Legend of Heroes series.

So its Dragon Slayer duology, Gagharv trilogy and the entire Trails series.

The The Legend of Heroes series is as big (in number of games) as the Final Fantasy and Dragon Quest series.

The First Game:  Dragon Slayer: The Legend of Heroes (1989) - playable on Switch via the EGG collection

The Second Game: Dragon Slayer: The Legend of Heroes II (1992) - playable on Switch via the EGG collection

The Third Game: The Legend of Heroes II: Prophecy of the Moonlight Witch (1994) - remastered on PSP as the second game of the Gagharv trilogy but its technically older than the next one.

The Fourth Game: The Legend of Heroes: A Tear of Vermillion (1996) - remastered on PSP as the first game , technically its the 2nd game of the Gagharv trilogy

The Fifth Game: The Legend of Heroes III: Song of the Ocean (1999) - remastered on PSP

The Sixth Game: The Legend of Heroes: Trails in the Sky (2004) - available on Steam and PSP, remake coming to modern platforms

The Seventh Game: The Legend of Heroes: Trails in the Sky SC (2006) - available on Steam and PSP

The Eighth Game: The Legend of Heroes: Trails in the Sky the 3rd (2007) - available on Steam and PSP

and the rest as you may already know lol