Ed,

There are very few airlines out there that will hire off the street applicants to fly as captain, and those that do probably don't have the pay or lifestyle that you are looking for. You pretty much are going to have to be "anybody's copilot" until you get some line experience, and odds of getting on at a major airline without some sort of airline experience (aka regional) is slim to none these days.

As for jumpseating, you sit wherever there's room these days. I haven't jumpseated in over a year since I'm no longer at the airlines, but most airlines now have so many "premier" frequent fliers that qualify for free upgrades that non-rev travellers and jumpseaters might as well expect coach, and sometimes you're lucky to get that with the number of folks that are flying on budget fares...

Out of curiousity how old are you? I only ask since you mentioned retirement... If you're above 60 fuggedabout it. Keep the Citation and fly around for dinner and golf.