Don't you remember Kirk in "The Naked Time" yearning for "a beach to walk on," an escape from the burdens and loneliness of command?
Yes, but I still can't see Kirk ever seriously considering leaving Starfleet. He knows the drawbacks to the life he chose, but he also knows, as Boyce said in "The Cage," that there is no other life for him. That's my take anyway.
I see Pike as similar to Sisko, a guy who really does want to escape the life he chose.
Let me put it another way: the difference between Kirk wanting another life and Pike wanting another life is, to me, the difference between a Greek tragedy and an English/Shakespearean tragedy.
In the Greek tragedy, you have a character meet a fate that is always destined to happen, and nothing anyone does can change it. So when the inevitable tragedy occurs, the attitude of the audience is, "It's too bad it had to happen that way."
The Christian/English/Shakespeare tragedy, colored by Christianity, says we make our fate, that if we follow the Christian teachings, we will be rewarded, but if we don't we will be pubished. So when something tragic happens in the English tragedy, the attitude of the audience is, "It's too bad that happened, because it
didn't have to happen that way." The tragedy is that the character's own choices led to his undoing.
I see Kirk wanting another life as the Greek tragic figure ; he may lament what he doesn't have, yet this was his destined path, no question. Pike is more the Christian tragic figure; his choice may have been wrong, that he should have simply made another choice, and that perhaps he still can.