I've been at wiscair (full company name is Pro Air Cargo and Consulting) since late August 2008 and really enjoy it.
The company president, DO, chief pilot, etc.. are all great guys, as are the pilots. We're a really small company. Six scheduled runs out of Anoka daily and two out of OSH, where the company is based. 15 pilots give or take.
It's primarily 310s flying bank work and hazmat out to the Dakotas (FSD, FAR, PIR, RAP, MOT, ABR) and charters, which are almost exclusively hazmat. We do have a 'van which usually goes to Fargo and also do that run in a 1040 (turboprop, unpressurized Navajo, basically).
The OSH runs go to IMT-ANE and up to SAW. The OSH guys don't have as much scheduled flying but do a lot of charters and are all pretty much part-time or doubling up doing administrative stuff.
Pay is pretty good, I think, for driving old 310s around. The airplanes themselves are well-used but well-maintained and I have total confidence in our mechanics. If stuff breaks, it gets fixed.
You're usually out in the morning, spend the day at the outstation and home in the evening. Crew cars and crash pads or hotels at all of the outstations, which is huge in my book. I'm writing this from my hotel room in FSD, matter of fact.
Um, other than that, it's part 135 freight in the upper Midwest in piston twins so it can be pretty tough work in the winter and a piece of cake in the summer, unless there's convection about.
I think in December I flew 53 approaches out of 110 total legs and in almost three years I think I've only had perhaps two trips actually cancelled. I've delayed a bunch and gone to different airports of course.
I really like it here. It's good, honest flying (if you like autopilots this isn't the place to be, although we are getting more and more autopilot airplanes) and everybody is really decent to work with.
If your're looking for turbine time this probably isn't the place. We only have a couple and it can take a while to get into one (I just started flying the 1040 last month) and there is a certain level of maturity required because you really are out on your own, making your own decisions much of the time. That latter part probably holds true for any single-pilot operator.
So, there you have it.