Yeah, it really sucks that just as the series was hitting its stride that Discovery cancelled it. Did the same with Stormchasers (although that was due to the understandable issue of fuel costs skyrocketing for the support/production crew).
As for Jim, he was very hands/is very hands on from what I understand. As they kinda alluded to in the last couple of episodes he kept track of every flight every day and ran the day-to-day ops, especially for the "small plane" operation that used to be Hageland (his company) and Frontier Flying Service. ERA is actually the smallest part of the operation being that it mainly services the hubs and a few large destinations (like Kodiak) from Fairbanks and Anchorage. However, as Alaska Airlines is moving more and more out of the regional operations (because the newer 737's aren't as suited to gravel strips), ERA is taking on more and more operations, getting more DHC-8's, and really becoming a full-fledged operation, so I'm not surprised that Jim's about ready to step away and let someone else who's "more capable" (not that he's incapable) step in. I'm sure he'll still have a role of some sort with the company and probably keep flying for ERA for a while, but he'll be able to take a more relaxed approach to it.

As for Ice Pilots, it's going strong on Weather Channel and Season 2 is finally being aired. From what I've heard, ratings are as good or better than their other shows, so I think it'll be fine there. The biggest problem now is that the cable channels have raised their expectations. When years ago a 1 or a 1.5 share was considered "spectacular" it's now a death knell. It's killed a lot of good, solid shows recently, not just reality TV. Hell, Eureka (one of my guilty pleasures) was cancelled this year and was averaging a 2+ share most of last season. This season it was even better but I'm sure NBC Universal just wrote that off as a blip because everyone knew it was the last season. Thankfully, there may be hope for a lot of shows because they're finally tracking DVR'ing of shows and using that towards ratings, and it's proving interesting for shows that they thought were low in ratings because they're finding a substantial DVR/Online presence. This may keep some shows in the future around now that they'll start taking that into account.