New to the Hitman series, question about challenges

I recently purchased a copy of Hitman 3 standard version. I do not own Hitman 1 or Hitman 2.

I have been playing the training sessions and Dubai. I’m currently trying to achieve all the challenges in Dubai and I noticed that for the Classics challenges the game is mentioning doing silient assassin multiple times up to 17 times. I have no idea how to achieve this.

You need to play each mission from previous games + current game in order to have them all.
There will be 20 something missions total in all 3 games.
You can buy H2016 and H2 Passes for H3 to do so.
I.e. you don’t need to buy two actual previous games, but some kind of DLCs of them for the recent game

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I see, thanks for the clarification. I shall move on to the next map then…

You always can leave any challenge for a later time, yes.
Have fun

My next question would be if I sign up for Xbox game pass and download the DLCs for the Hitman 1 and Hitman 2 content for free, will I keep these DLCs after my game pass expires?

No, the license for the DLC is tied to your subscription status or purchase history. If you let your Game Pass subscription lapse, you will not be able to access any games or DLC tied to the service and you will need to either renew or purchase.

This also holds true if a game (and DLC) is removed from the Game Pass service.

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