ORIGINAL: NorfolkSouthern
Get the trainer first, get good at landing. Get the G3 flight sim, and practice practice practice. Then, get your low-wing trainer (they're actually quite nice, and reasonably fast too). Keep both of them, you want the trainer for utility purposes and the low-wing for knocking around. Then get the flying motorcycle with the second mortgage as long as you don't take blood pressure meds. If you ARE prone to high blood pressure, the big bipe with the bike motor's gonna raise that a few notches. I hope this helps some.
NorfolkSouthern
Got the trainer already. I've been playing with the Cockpit Master software, but frankly it is not that great. Often crashes to the desktop. Also, since it is the "Hangar 9" version I am sure that the developer won't be much help. Everyone recommends G3, but it is pretty expensive. $200 is pretty steep for what is essentially a video game. Plus, no Mac version. If it was $49 for a bring your own transmitter version I would jump on it.
Message heard though. Need practice.