Delta-apply 24 months from your planned terminal date if you’re retiring, or 12 months from when you’re getting out. Find a buddy who paid money years ago for a Delta App Review. Look at how he worded stuff, and just “do that.” No need to spend the money. Or search the forums, or post the question, I’ll answer it.
United-I think they’re still at 12 months across the board. So I would apply around 14 months out and expect a call around the 12 month mark or closer to retiring/EASing. While you’ve still got a jet or the equivalent and the ability to XC, get one of your buddies who flies for UA to arrange a Chief Pilot sit-down. Fly out and do it; they’ll know how to schedule it.
American-I think they’re still 12 months so copy United’s recommendation.
SWA-contrary to what I’ve heard about military guys getting interviews at 14-16 months from getting out, I literally spoke, on the phone, to the head of HR. Long story as to why but when you have an interview, you HAVE to be 12 months or less from terminal or EASing or the CJO expires and they won’t be thrilled. But keep in mind, unlike Delta who gives you 7 days after emailing you to take the online assessment, and if you pass, they then send you a link with available classes for your application month. The furthest interview date from that is about 7-8 weeks, so you could do the math somewhat and back-up your timeline. SWA gives you 60 days from the day they offer you an interview to SCHEDULE the interview, and every week you wait those interview dates available can be further and further out. SO, you could apply at about 14 and easily have one within 12 months of retiring.
UPS-know someone, not hiring. FedEx-know someone, not hiring.
As for attending conventions, paying money for people to see you, if you have “substantial” military time and you have internal LORs from your 20+ of aviating, save your money. You’ve paid your dues, and if you’re organized and can apply in the above timelines, you’ll have a job. I just don’t think you need to waste money to be recognized; if you’re low time low quals maybe, but if you’re retiring after 20, skip it skip it. Your resume likely speaks volumes and, while I can only my speak from personal experience, you’ll have no problem getting an interview. Invest in yourself with some interview prep, ANY prep, and you’ll be right where you need to be.