Kylo with calculation and advanced optics? Or a another squad mate with it? Does that help trigger the dark side condition or is it a waste of ept?

If you're taking Kylo Ren, then someone capable of reliably causing a critical hit is not a bad idea.

Imperials, however, are not short of ways to do this without resorting to specifically buying an EPT for it that messes up his ability to act as an expensive high PS or high action economy ace.

• Backdraft or Darth Vader (or any other Advanced Targeting Computer TIE/x1) are similar cost (okay, cheaper than a tooled up Kylo Ren, but not much cheaper) 'ace' wingmen
• Rear Admiral Chiraneau gives you a nice hefty 'command platform' for ace-support crew to stand on, and still have a turret which can reliably set off Kylo's condition.
• Omega Ace with Advanced Optics, or Winged Gundark are cheap 'filler' ships that can reliably cause critical hits.
• A Gunboat with Proton Torpedoes is probably going to cause a critical when it fires

I don't think you'll really fit a silencer into a classic Imperial 'triple ace' list, because a kitted out First Order Vanguard Silencer is just too dratted expensive. But if you get Kylo/other ace/pocket ace or Kylo/Decimator, then making sure at least one of the above is in the squad is not a bad idea. Vader and Chiraneau arre good ships anyway, even without their abilities complementing Kylo's.