One of my favorite series! Played all 5 games that made it to the west.

My boyfriend got into the series last summer, and I've played through all 5 games that made it over here (Sky 1, 2, 3rd and Cold Steel 1/2). Waiting on the superior fan translation for Trails to Zero before starting it or hoping xseed (or someone) will conjure a PC port out of nowhere. There's supposedly a questionable, but functional, fan translation out there.

For those starting with the series, chronological order (Sky-->Zero/Azure "Crossbell"->Cold Steel) is best but you can start with any sub-series. PC is currently best way to play each game, with the 3rd being PC exclusive. But, for a given subseries, do go in order. The main reason to play the series is the world/lore building. The countries each subseries feels very down to earth, and seeing countries (both from within and viewed from others) creates a storytelling that feels very real. Being a JRPG, there's plently of anime tropes to go around (like a certain organization's existence); however, because of how all the games are related, there's really no series that makes you feel alive in the world quite like Trails does. Also, if you do play, do talk to the NPCs. They update their dialog all of the time so they are another lens into the world building.

Also, for TC and others who have played through Sky SC:

(SPOILER)

Who do you think is the grandmaster?