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I have finished all 3 games of trails in the sky and I loved them.
I will definitely buy the other series, now comes cold steel and I heard that there is one more which might be released some time. (Sorry, I dont speak japanese so I have to wait for a translation.)
some questions:

While I loved all three trails in the sky games, I like the gameplay of the first two games (mix of towns, open world and dungeons with lots of people to talk to and lots of side quests) much more than the 3rd (dungeon crawl with sidequests as "lore dump". The contend of the doors in the 3rd was very interesting, but having tons of reading as "side quest" when the rest of the game is mostly fighting felt strange.
Is cold steel more like 1st and 2nd chapter? What about the other parts of the trails series that will (hopefully) be released later?

I know this takes place in another country than trails in the sky (Erebonia). Will we meet some people again?
Like they were a playable character in one game and an NPC in the other?

About the timeline: Does this play before, after or at the same time as trils in the sky?

Does the game end with a cliffhanger and part 2 and 3 continues were the game before ends (like chapter 1 and 2 of trails in the sky)?
Is cold steel more like 1st and 2nd chapter? What about the other parts of the trails series that will (hopefully) be released later?
Cold Steel is very much like Trails in the Sky FC. The only difference is that instead of travelling from region to region, you have a "home town" you return to at the start of each chapter, then go on field studies to different towns/regions throughout eastern Erebonia. Cold Steel II is kinda like SC where you end up revisiting most of the locales the first game introduced.
I know this takes place in another country than trails in the sky (Erebonia). Will we meet some people again?
Your playable and supporting cast is all new, but yes, you do see a handful of characters who were introduced in Sky.
Like they were a playable character in one game and an NPC in the other?
Cold Steel II has one playable character who was introduced in one of the books in Trails in the Sky FC.
About the timeline: Does this play before, after or at the same time as trils in the sky?
It takes place in the year 1204 of the Septian Calendar. Trails in the Sky FC started in 1202 with Trails in the Sky 3rd taking place in 1203. So Cold Steel starts about 2 years after Trails in the Sky FC started.
Does the game end with a cliffhanger and part 2 and 3 continues were the game before ends (like chapter 1 and 2 of trails in the sky)?
Yes, Cold Steel I ends in a cliffhanger that's worse than the one in Trails in the Sky FC. Cold Steel II (which has been confirmed for PC) doesn't end in a cliffhanger, but quite a few story threads remain unresolved. The upcoming Cold Steel III which will release in Japan in under 2 months is set to be the finale of the Erebonia trilogy.