My advice would be to narrow down the location on Kodiak you want to hunt by looking at harvest stats and average skull size. Some areas consistently produce better bears than others. Yeah, I know, a big bear can be found in any unit there, but some areas are much better. Then, once that is decided, book with the outfitter for that area.
If you don't want to wait several years, assuming it's as booked up as Jake's, then head to the Peninsula as it's open each year (alternating spring and fall) without tag limits. Some great options over there as well.
My experience with hunting fall bears on Kodiak is a bit different than most in that I had a great tag for an area with lots of bears. We saw over 100 bears in our 15 day fall hunt. They were everywhere. Do your homework and go with the best, it's a lot of money for a NR to invest only to end up going with a subpar outfitter and don't kid yourself, they certainly exist. I am headed down this fall to hunt the Aliulik pen on the southern end of Kodiak, another dream permit and I have a feeling it'll live up to it's hype.
I don't believe there is a comparable hunt on on the planet (maybe DG in Africa) that can give you the adrenaline rush that hunting brown bears does. Hunting them and getting close gives me the "buck fever" (though controllable) like I haven't felt since I was in my teens. There is nothing like it... Good luck with your research and best of luck when you go.