I've been doing this kind of work for almost 7 years now. Being in the right place, at the right time is what got me the job. In a nutshell, my previous company in Alaska had four Casas that were sold out from underneath them by our parent company. I immediately called up the new owners and offered my resume. Never heard of them, but they were called Blackwater Aviation. About a year later they got the contract in Afghanistan and I was hired.
A month after that I picked up one of their planes in Australia and flew it into Afghanistan. Stayed there for a couple years, then started on a contract in Africa. Stayed there a couple years, went back to Afghanistan. Stayed there a couple years and I now I'm back in Africa again.
All that being said, getting hired in these jobs is really right place, right time, along with a lot of who you know. My company AAR (Blackwater Aviation was sold early last year and no longer exists) has been trying to get away from the who you know deal, but so far that hasn't seemed to produce too many good people. You're best bet is to submit resumes, hope for an interview (or at least to meet someone with enough authority to hire) and keep in friendly contact, not being a pest. But really the best way is to have someone in good standing with the company that's flown with you and willing to vouch for you.
As far as working conditions, it varies. For the most part, you can expect to stay in either a B-hut (plywood walls) or a tent. The first year of my second tour in Afghanistan was in a tent. The last few months were in a Conex. Our company is doing mostly 60/30 rotations, but there are some that are getting 60/60 and I think maybe 45/45. Other companies (Dyncorp for sure) are doing 6 months/13 days.
Pay is normally based on a daily rate and may or may not include a per diem. My company will only pay per diem if it's required by contract. The Afghan contract does not require it. The good news is that Afghan per diem ain't much anyway.
Due to IRS having new interpretation of the rules, and their resultant crackdowns, the days of 1099s is coming to an end. At AAR, we're now all W-2 employees. Depending on your situation, it can be good or bad. If you play your cards right, it's possible that you can qualify for the Foreign Earned Income Exemption. This is worth roughly 90k+ being knocked off your taxable income. See your CPA for details.
For special training, if you go to Afghanistan, you'll need to take a CRC course. This is mostly classroom, but covers SERE topics, cultural stuff, combat medicine and weapons training (M-16, M-4, AK-47, 9MM). It last a week and involves a detailed medical examination.
As far as risk over in Afghanistan goes? Well, it's a war zone. What can I say? There are bad guys that want to kill you. For the most part, you'll be held prisoner on the base. Unless you go over as a truck driver, don't expect to ever get off of a base as a civilian. As a result, you'll have very little exposure to the general population, however rocket attacks happen quite often. Mostly these are harmless, but they do kill people when they fall in the right spot. Not much you can do to mitigate that risk. Good news on this is that for the most part, when you find out about a rocket attack (hear it, red alert, etc.) it's over with. There are exceptions though.
As far as planes getting shot, our helos get shot at all the time and get hit from time to time. The Casas are also low flyers and get shot at quite often. Fortunately, the Taliban fighters are lousy shots, but our planes have picked up some bullets from time to time. The high flyers are out of small arms range and don't get bothered. The "stinger" threat is minimal for various reasons.
Fortunately, we've never caught anything that caused us to go down (although we did lose a couple helos in Iraq a few years ago). Just takes a while to do the sheet metal repairs. Most times when I got shot at, I didn't realize it until a passenger mentioned it to me later. However, there was one time when I was back taxiing for departure that a mortar dropped in front of me. It was right on centerline and just off the end of the runway. This resulted in my first and only emergency takeoff. I didn't feel like hanging around.
To help mitigate the risk when landing, I typically will either come in steep (like 2000-3000 FPM) or fast (180-200 knots until a mile out) and put the brakes on at the last minute. The Casa is real versatile when doing this kind of stuff. Also, takeoffs are done either max performance (to get altitude over the base) or low level departure from the base and a zoom climb after getting away from the area. I try to mix it up and varied my technique based on what I felt was necessary at the time.
Whew!! I think I answered most of the questions in this thread. Y'all have fun now!!
BTW... I'm pretty sure Teller's friend works for us. There's only two Dash 8 operators in Afghanistan that I'm aware of. I don't think the other guys take two load masters.