South side gets pretty flat in the winter though,you'll probably have to drive somewhere when december comes,or take the bus(one of the best bus systems in the country, and I seem to recall that you can take a board.)however south side seems to always be rideable if you have a big enough board.
haha yes you definitely should be! I went last summer and I was on Kauai and the big island. Its just cool to be there because most of the people are either surfers or super laid back. the aloha spirit is definitely true because after being there for a week you start to talk like the hawaiians. make sure to befriend a local - you'll learn a lot!
Ya man you're asking about Oahu, where surfing pretty much started. Duh there's waves therer year round. I went a few years ago in June and depending where i went it was anywhere from waist high much to about two feet overhead and hollower than most east coast waves. So, ya its not the north shore, but theres gonna be some fun spots whether your a novice riding a 9ft bz softtop or an expert.