Don't know about PennAir, but keep in mind Era/Hageland is the airline featured in the Discovery channel TV show "Flying Wild Alaska." It's a pretty fair bet that they're sitting on a huge stack of resumes.
If you're really interested in Era though I suggest you go over the interviews section of
http://oddballpilot.com/ with a fine tooth comb. Aidan seems like an outstanding guy and has done a tremendous amount of legwork in sitting down to so many managers and pilots at so many awesome non-traditional companies. Aidan if you read these boards, THANK YOU!
There are at least 3 employee interviews with Era/Hageland employees and managers on that site (including an interview with Mike Hageland from last month that I haven't gotten to listen to yet), almost all people recognizable from the show. In one I seem to recall the C208 FO position being described as an apprenticeship... preferably as outreach to the local people (there's at least one guy on the show who is Inuit and became a Caravan pilot)... pay sounded extremely low, but it's a put your time in with the company and let them get to know you and move up kind of deal. Caravans are single pilot airplanes, so the FO position is not a required crewmember, it's a let them get to know you and show you the ropes before letting you loose in Alaska in a Cessna 207 kind of position (from what I recall in the interview).
So if you're dead set on Era, spend some time on the oddball pilot site, set aside some hours to listen to all the interviews (they're all 30 min - 1 hour each) and get as informed as you possibly can about what you'd be getting yourself into and what you can do to make yourself competitive. In Alaska, this usually means buying a plane ticket up there, knocking on doors and making calls until you are able to actually physically hand your resume to the person doing the hiring... NOT emailing it to them.
But I'm just a guy who has given this career change some thought. Don't take my word for it, talk to guys like
Roger Roger and
ASpilot2be who actually do it for a living.