I have owned two wooden cruising boats in my career. Disregarding brightwork, I found the maintenance of a well built wooden hull to be not a whole lot different than fiberglas. I did have to do the periodic paint job which was pricey, and I did have some deck issues that required maintenance and replacement. I would have no qualms about owning another wooden hulled boat.
That said, Alaskan's are great boats, well designed, well built but as with any boat of that era, maintenance is the key. Pay more for a well maintained boat of a good pedigree and you should be fine. Like most Grand Banks, pay attention to fuel tanks, deck condition, windows and like most wooden boats, fastenings, rot and general maintenance.
Bottom line: do not dismiss a wooden boat simply because it's wood, dismiss any boat that has not been maintained.