I've been posting in a variety of places to get maximum exposure

I also posted 2 1/2 weeks ago, since then I've had a lot of information gathered and have less questions just different ones now.
I just want to see what I can/when I can, I am not in a rush/hurry and I don't have much particulars so I'll do what comes and goes.
My concern is lodging for the high peak of the summer June-August, I plan to utilize hostels where available and cabins where available as well.
I would like to start off in Ketchikan since I'll be coming from Oregon and I'd like to see how far I can get from Ketchikan June-Dec; I should be spending roughly a week in most significant areas for example: I would stay in Ketchikan for a week but also visit Annette Island once or twice as needed.
I've been doing a lot of looking around, and noticed on Google Earth (which gives more details than Google Maps could ever) there are quite a bit of islands nearby Ketchikan other than the obvious (Gravina) island where the airport is, there's Danger Island, Pennock Island, etc are all these islands worth visiting?
Then I would move on and head up to Craig and visit the communities on that island for a week or two as there seems to be more to cover there, hard to tell as Ketchikan is quite big too so I'm not sure if I would see it all in a week.
I know there are not hostels everywhere so I'm looking to see what my options are: couchsurfing for 2-3 days here and there while I wait for an opening at a hostel or cabin or some other accommodation arrangements. Perhaps trade for lodging & a small bit of food for some volunteer time, etc.
My GUESS is I could make it to Homer or Seward by Christmas and then fly back to Oregon at that point, I can't really predict how long it will take me to see everything in 6 months which is to include island hopping (the ones worth hopping to).
My concern with winter is survivability, Oregon gets cold I do have warm clothing for that kind of thing just not sub zero

. The other thing is getting around during the winter months, I'm going to guess this isn't easy to do? And finally, airline service during the winter months will I have difficulty getting flights? Obviously bad weather affects everyone not just Alaska.
Hope you can help! And TIA for your time reading!