Been reading from a distance, and think you are all too optimistic with Bellerin. One, dont underestimate his love affair for Arsenal. He has constantly maintained no desire to leave, and has a great relationship with Wenger and loves London. Two, he wont be sold anytime soon, and if he does, he will be channeled back to Barcelona who also want him.
You may cite the Pep factor, but Pep seldom stays too long at clubs. Its generally 3 years wherever he goes. By the time Bellerin contract is coming to end (baring him signing an extension which is likely), Pep's 3 years will be nearing end.
We heard it before the season started and nothing became of it. So why anyone would assume a January transfer is possible,?
"Clubs", by which you mean two, the first of which he was youth coach before being first team for four seasons. Not a great sample size.
The only question Bellerin has to ask is would two seasons under Pep do more for him than two more seasons under Wenger, or two seasons at Barca. If yes he will come, if not he wont. I don't think any player, even those who have come to us to play under Pep, see themselves playing under him their whole careers.