Don't be intimidated, it's not that bad to plan once you get started. I started putting together our September trip last November, and 9 months was more than enough time to iron out all the details. We did a drop hunt out of Kotzebue in Unit 23, non-guided. There's a thread on here somewhere with pics. I've got an app in now for 2015 Moose in the same area.
If you're doing a drop, get a spot reserved with a pilot the previous October/November. The good ones book up quickly.
The biggest hurdle is the logistics of getting your harvest home. Most years Alaska Airlines stops allowing antlers as checked baggage around Sept. 1st. Plan to ship antlers home in a big box. We brought up a stack of empty rubbermade 30gal totes, checked as one luggage piece on the way up. We filled them with our boned out meat and paid extra baggage fees for each on the way back. It wasn't bad at all and they were totally cool with it. As long as the meat is inside a tied garbage bag inside the tote.
If you're looking to do the Haul Rd. thing it will be cheaper and easier to plan. I was going to do this, but I'm glad we went the bush plane route. That was incredible and we were miles upon miles from any other hunters the whole time.
The WACH migration has been later and later each year for the past few. I'd recommend going no earlier than Sept. 10th. It will be cold, but that's what you want in order to see good animal movement. Also the bugs will be dead and meat will keep well.
Post up some more specific questions, I'd be glad to help answer them.
