Blackra1n was originally a tethered jailbreak solution, but that is no longer the case. I just recently jailbroke and then unlocked (with blacksn0w). Very easy. For instructions (one among many places) is:
Early November can be a very pretty time in both areas. The majority of the larger tourist groups will be gone. It shouldn't be particularly wet though evening temperatures could drop so be prepared with some warm clothing.