About Dean never finding his father, I don’t necessarily think that is reflective of Bae/Rumple’s situation. Dean was a character…if they had named the Mystery Man Dean Moriarty, then, I would think along those lines. But, Neal Cassady being the ‘role model’ for Kerouac’s character is just one small part of the real Neal Cassady.
Neal was also the role model for the character ‘Mac’ in the movie “One Flew Over the Cuckoo’s Nest”, and while they did nod to that movie on OUAT, the character, Mac doesn’t really have much to do with the Bae/Rumple situation, either.
I believe K&H weren’t pointing at the ‘characters’ associated with Neal Cassady so much as the real person.
I posted before: Neal Cassady was also known for the documentary “Magic Trip” along w/ The Grateful Dead, where Neal drove the ‘Further’ bus from San Fran to NY. He earned the name Cowboy, and The Dead wrote a song about Neal and the trip, “The Other One”. A line in that song: “Cowboy Neal, at the wheel , on the bus to Never Never Land”.
The trip itself ties in with NY.
The bus ties in with the Peter Pan Bus Co. based in NY.
The Grateful Dead ties in with the Geronimo Jackson clues- sticker on Emma’s car, CD in Henry’s backpack, sticker on Neal’s phone.
Geronimo Jackson is a fictitious 60’s band, based on The Dead, created by K&H for LOST.
They also used the name Dean Moriarty in LOST on (Ben’s) passport, but the use of the name was not reflective of that character’s situation, either.