It wasn't a boat based hunt, but my nephew and I did a DIY drop camp on the south end during the last week of October in 2022.
The wind is NO JOKE there! Plan on having wet weather. These don't look like much, but they were worth their weight in gold for keeping my hands dry and warm while maintaining reasonable dexterity:
https://www.kinco.com/products/featured/winter-wear/1886P.html
You can probably find them, or similar, on Amazon.
As some have said, the consensus for that time of year seems to be that most of the better bucks are still up high - barring significant early snowfall. From our trip, I don't disagree with that; however, I managed to take a good buck (95") low during that trip, ~500 ft - so, it can happen.
Trekking across the tussocks is every bit as miserable as people claim - especially with a heavy pack; though you may not experience as much of that on a boat based hunt as what we did being dropped more inland.
There is one guarantee... Kodiak is a special place, and you will have an epic adventure you'll not forget. I'd definitely recommend it if you're able!