I used to read some dark horse comics in mid 90s that were like 1000s of years in past and I think that actually worksso much better for anything prequel-ish. I’m sure they aren’t considered canon but some aren’t bad, I think same series had novels.
For jumping ahead it’s hard to say. Is it better that known heroes are just old people like lando/han/leia/Luke in recent movies or better that Luke is some legend from many 100s of years ago.
In the walking dead comics there is a 10 year time jump that is awesome. They couldn’t do it on show and keep cranking out episodes and I think show would have been better off actually taking 10 year break at its peak and coming back accurately vs what happened.
For the real nerds out there, people love the Old Republic video games. You probably can't quite make a show out of them, but honestly I can clearly picture cutscenes with old Mandalorians at the height of the culture and man it was awesome. But I was thrilled to just see something else.