Hi. The best way to break into Alaska bush flying is to be in Alaska.
Right now there is a huge shortage out in the bush. Everyone has left for more cushy jobs down south.
The lifestyle can be pretty relaxed or it can be a lot of work depending on where and for whom you work.
Sorry for the real general answers. I can't really offer you any advice except to come here and meet some employers and see what they offer you. Here's a partial list:
Peninsula Airways
Bering Air
Cape Smythe Air
Hageland Aviation
ERA Aviation
Grant Aviation
Frontier Aviation
Warbelow Air Service
Arctic Circle Air
Good luck. Please feel free to follow up.