Good grief man, you're going waay out there. If you're considering devils elbow or Kadake... have you thought about taking the Ferry into Kake and getting a skiff from there??
If you are that far out it might be an option. I have no clue about skiff rentals in Kake though. Flying is a good choice......
Yup, Devil's Elbow. Since it is nearly impossible to get to, I have no problem telling people where we are going. It is that hard to get to. I have all the nautical maps, and given the shallow/rocky nature of that pass, I can see why no big boats want to go in there. And why many have cautioned me about the tides creating some serious whitewater in the narrows and not to get caught in those with a skiff..
Given all the research I have done, I would probably have done it differently, saved logistical headaches, and saved money. Here would be some other places I would look if I was doing this:
Any of the Prince of Wales cabins
Portage Bay
Saltchuck
Castle River and Flats
Towers Arm
Brieland Slough
Beecher Pass
Kah Sheets Bay and Lake
Steamer Bay
Berg Bay
West Point
.........and probably a hundered others that would be easier options to get to.
All of these places have great bear hunting. Locals tell me it is not what it used to be, due to increased hunting pressure, but a look at the record book shows that many 20"+ bears have been shot on these islands in the last five years. Like most hunting, it will just take more work and effort, which is why it is so much fun.
Most of the cabins (not all) I mentioned above are $25 per night and you can fly to Petersburg and rent a skiff to get to them. Skiff rental is about $140 per day, with a boat that can haul 3 guys and all their gear.
Split that out three ways, and a week of SE AK black bear hunting costs $385 per person. Not counting food, license, and travel to Petersburg, Kethcikan, or Sitka. You are eating if you stay home, and if you go guided, you are going to have travel and license costs also, so that is why I haven't included those for comparative purposes..
Pretty hard to beat an experience like that for $385 per person for a week. Travel to any of SE towns via commerical airline (Alaska Air) runs about $500 round trip, depending upon when you make the reservation, etc. License ($85) and tags ($225) combined are $310, and since you are there, you may as well pitch in for the $55 one week fishing license. All of them are "over the counter" so no worry about drawing a tag.
If you can have more fun during a week in May than black bear hunting in Southeast Alaska, let me know what that would be. Especially for less than $1,500.