I joined mcseal2 on this hunt, and figured I would share a few of my own lessons learned/observations, especially around logistics. I'll add the same disclaimer - this was just my second Alaska DIY hunt, and there are others on here who know a lot more than me!
Gear - I focused on "warm" and "dry", and was very happy I did. I took two sets of Kuiu rain gear - Yukon and Kutana - and hunted in the Yukons and kept the Kutanas as a dry set for camp. I generally hunted in First Lite base layers, a Kiln hoody and rain gear, and then for glassing and warming up had a Kuiu Superdown Pro jacket and Superdown Ultra bottoms. I also had a Kifaru Lost Park parka for evenings at camp. Even when it quit raining, it was never dry enough to hunt without rain pants - the First Lite Corrugate pants I took never got used.
Island Air - The operation at Island Air was top notch. They were easy to deal with in booking our trip and promptly answered questions. As mcseal2 said, weather delayed us getting out to the field for two days. The folks at Island Air were transparent about the delay, kept us updated, and were excellent to deal with in the process. Pilots and aircraft were great, and it was nice to be working with an operation that had multiple aircraft available as they worked through the backlog. I provided weather updates via InReach each morning and also coordinated on our pick up timing, and Island Air always responded right away to texts (it is nice to know the people in charge of getting you out safely are paying attention!).
Commercial Flights - Alaska Airways is the way to go. They have more generous baggage weight/size allowances, and their people are used to dealing with hunters and everything that goes along with that. We had the option to book the flights direct with Alaska Airways or through American Airlines as their partner. Either way would be the same aircraft and schedule, but if we had gone through American, I believe we would have paid more for oversized and overweight baggage.
Lodging - I highly recommend an airbnb/VRBO rather than staying at one of the Kodiak hotels. We've done this for our last two Alaska hunts (Kodiak and Kotzebue) and both were good experiences. During our weather delay, waiting around was much more comfortable from our own little house with a kitchen and living room than it would have been in a hotel room. It was nice to be able to cook a few meals, have space to prep and sort gear and then process meat upon our return. For 4 guys, the price was essentially the same as a hotel.
Getting Around Kodiak - Taxis are plentiful around Kodiak, and there are several that are vans or trucks that can take multiple people and gear. There are several companies, but we found one driver that was great and just texted them directly when we needed a ride. Depending on where you stay, you also may be able to walk to several of the restaurants and to Big Rays sporting goods.
Kodiak is the most challenging place I've ever hunted - the weather and terrain are fierce, for sure. It was an amazing hunt, and I can't wait to go back!