Will your future self live with this?
A good technical tradeoff analysis is about whether your future self is willing to live with the solution.
Say you are analyzing a problem and you have two solution options. Option A is technically superior to B. It's more novel, has new technical challenges that the team didn't face before and overall is more interesting to work on. On the other hand, option B fits right in the current system, but it lacks all the fun stuff.
Now imagine a year from now, half of the folks who built the solution may not be here anymore. Tech stack changed. New projects on the plate to work on. You need to occasionally wake up at 3 am to solve an incident because no one else knows how to deal with this. Do you still believe A is superior?