1. what do you corporate folks like most about your job?
I spent 11 years at the airlines (regionals, LCC, and major) and never imagined that I could find a flying job where I could be home almost every night. I was always under the impression that corporate jobs meant living on a pager, no set days off, and keeping the resume up-to-date because you never knew when the airplane would be sold.
I am fortunate to have found a job with a corporation with a director whose philosophy is, "Work to live. Don't live to work". We have a set schedule of days off, trips that rarely get back after 17:30, and no pagers. I love watching my son grow up instead of hearing about it from my wife on the telephone from some hotel in Rochester.
I suppose we need to determine what it means to be a "successful" pilot. I used to think it was flying the biggest metal for the biggest paycheck. Now I think it's flying as little as possible for a reasonable paycheck.
2. What's the biggest pain in the ass?
Not so much a pain in the butt, but I miss having an APU. Sometimes when you're out in Podunk USA and there is no GPU available you just can't do anything to cool the airplane down. Nothing worse then climbing into a 140 degree cockpit and try to get airborne without passing out.
I also miss having a dispatcher. Fltplan.com is a great website, but when the weather is going down across a whole region, sure would be nice to have someone you can call and say, "find me an alternate and figure out a fuel load for me".
Finally, deicing. At the airlines deicing was very standardized from the radio communication to deicing crew performance. In GA it's a crapshoot and that's frustrating.
3. What would you have done differently to get where you are now?
Would have skipped the airlines entirely. I wasted 11 years of my life building qualifications that meant NOTHING to corporate employers. In fact, worse than nothing. Some of them stayed away from airline pilots like the plague.
I would have done the CFI thing until I had 1500 hrs (135 mins) then flown freight for a large company like AirNet or Ameriflight. Transitioned to turboprop or jet in those fleets. Pound the pavement for a CORPORATE (NOT 135) operator that flies similar aircraft or go to a fractional like Flexjet, Avantair, or NetJets and then network, network, network. Talk to corporate (not 135) guys at the FBOs and develop friendships.
My final advice? Stay away from 135 if at all possible. It will present an inaccurate picture of what flying a corporate airplane is supposed to be like. Try to aim for the top of the Fortune 500 list.
Good luck!