Not all Alaska operators require Alaska time. K-2 Aviation in Talkeetna for one, Island Air in Kodiak for another. So the "insurance" requirement for Alaska time is not written in stone. Also, many of those operators who prefer Alaska time, are willing to accept equivalent experience i.e. mountain time. If you have no Alaska time, but have a few thousand hours logged, especially in type, you're not going to be turned down for lack of Alaska time.
FARs part 135 does not authorize a pilot to fly as PIC unless he has an instrument rating with his commercial certification and a minimum of 500 hours TT. Of that 500 hours, 100 hours has to be cross country time (over 25 miles from point of origin) and of that 100 hours, 25 hours has to be at night. Most Alaska operators require 1000 hours or more, some time in type, and most of them like to see some Alaska time as well.
K-2 Aviation requires 2000 hours and prefers pilots with a substantial amount of tail-dragger time, especially Cessna 185 time, but they do occasionally hire pilots with no tail dragger time. Most of the pilots flying for K-2 have been with them for many years and return season after season to fly the mountain (McKinley) from April through September. But there is often a slot or two open with them at the beginning of each season.
Island Air in Kodiak will sometimes accept new pilots with only the 500 hour 135 minimum experience requirements.
Airline experience provides you with hours logged, but may not be helpful beyond that in getting a "bush flying" job.
Floatplane operators are looking for a couple of hundred hours on floats...again this is probably an insurance requirement. But, a way around it is to try and find a job with a company that uses both wheel planes and float planes. Hire on as a wheel pilot and as a company pilot, phase into floats on an insurance waiver.
Lodges tend to hire high time float pilots, but do provide room and board and pilots probably average around $6000 a month during the season (May-September). Most of the remote lodges in Alaska operate under FARs part 91, but under special rules for Alaska only, are allowed to fly beyond the 25 statute mile limit imposed on other commercial operations working under part 91.
Airtaxi operators vary widely in their salaries and flight schedules. There are some outfits in Southeast Alaska that start their new pilots at $25 per flight hour. Generally speaking, the further north you go, the higher the pay, and of course it increases with experience and years spent with the company. Some operators provide only occasional days off during the busy months. Others offer scheduled days off and some even have a two-week-on-two-week-off schedule. A few even have retirement plans. Many offer medical coverage and many don't. The management styles for different Alaska air taxi operations vary from almost intolerable to very respectful and everything in between.
"Almost intolerable" covers a lot of ground and can include working for someone who has the personality of a wounded rhinoceros, or an outfit with shoddy get-by-with-as-little-as-you-can maintenance. There are owners who push you to fly in really lousy weather(not as prevalent as it used to be, but still a factor). Other bosses will have you doing menial work (digging new cesspools, building trails, being a janitor etc.) when the weather prevents flying. Lodge owners are especially prone to that scenario.
So, select your Alaska flying job after acquiring as much information as possible about working conditions.
www.flyalaska.com has plenty of free information including a directory of Alaska flight operations and a message board/forum. The membership section has updated specific job listings and a bunch of other info including website links to over 200 Alaska flight operations.