You've made goods points TB.
Another old show that relied heavily on a similar premise by the use of flashbacks, to great effect, was the 1972 tv series
Kung Fu with David Carradine as... "Kwai Chang Caine, a Shaolin monk who travels through the American Old West, armed only with his spiritual training and his skill in martial arts, as he seeks Danny Caine, his half-brother."
It could be a very compelling form of story telling by filling in the missing pieces of the past, while he's off on new adventures. And, it donned on me... we have also been exposed to Mando's back story throught the first season by a similar flashback style.
What would JFDF do? It will be interesting to see how they approch Boba's character who has such a rich history, while providing him with an arc that moves his development forward, as just a simple man trying to make his way in the universe, among other things.
Honestly, with John & Dave, I think it's in good hands.