Wow. Too many to choose from.
Props- The incomperably LOUD Vickers Viscount. Oh to be with UAL in 1964.
Classics- I'd stick with the DC-3
Airlines- How can one choose between the 707, Caravelle, Convair 990 and last, but not least, the original RJ, the VFW 614? (look it up)
Bizjet- Already flown the Gulfstream and the X. Tough choice between the MBB(HFB) 320 Hansa Jet and the Lockheed L-1329 JetStar. Forward swept wings vs. 4 friggin throttles on a bizjet. Damn. Again, born 30 years too late.