@op: Have you considered hiring someone who develops AIR applications for the client software? I'd imagine AIR developers are more in the YC-Hacker-mold because the boring things mentioned above are abstracted by the runtime.
All except the look-and-feel bit. Mac users want apps to have the Mac look-and-feel, though perhaps Windows and Linux users aren't as adamant about it, so maybe a Mac-ish look-and-feel can be the common denominator. Also many users wouldn't want to install the AIR runtime.
Either way they have to install something (either your app or the AIR runtime). At least installing the AIR runtime once, gives them access to other AIR applications as well.
