DO IT !!
What are you waiting for?
I'm waiting to decide how much I want to give up half of my vacation.

Don't you get bored flying to the same airports up in AK ??
It's hard (for me) to get too bored flying a twin turboprop into narrow, ice covered, gravel runways, a number of which are surrounded by high terrain that you descend past and around. And that's just going into my normal run. I have one of the only two lines (they alternate) that are consistant, most guys do prefer different airports every day. And I still havn't gone into all of the airports our 1900s will go to (I do go to different places occasionally) and charters can send us anywhere. Even Anchorage can keep exciting. For the last few days the winds have been consistantly 20G40 kts on the ground with higher winds aloft down there.
Remember how big AK is... it's like I'm flying around half of the continental US on a regular basis.

I'm still thinking about it. I'll at least get some info from him and see how serious he is and stipulations etc.
Thanks for the input guys.
Hey Chicca, volunteer to ride along and you might convince me.

Regarding Mike's comment on taking someone along, that's the only way I'd do it. In my opinion, dual pilot really is the way to go for long trips.