@zippy Concur. Hence my statement that pay should be a critical driver while you grind it out there.
I agree... there seems to be this myth that everyone can get off active duty and spend 12-24 months flying on the outside and they'll be scooped by the major of their choice once they've done their penance.
It has happened that way for some people, however there are plenty who haven't had it work out like that and the question becomes how long after their last flight on active duty do they transition from "desirable military pilot" to brand x regional/135/91 guy who has some military in their background.
There's no clear cut answer- I was sitting at lunch the other day with a dude who retired as an O-5 from AD in a flying billet who can't get a call from the majors while the JO SELRES IP whose been flying outside for 2 years is lamenting that he doesn't want to leave his Job and go to the airlines right now (but his spouse is making him do so) and got interview invites from UAL, DAL and SWA and is trying to push them back a bit longer.
I don't think that 4-6 years is too long for a Helo guy to plan to be at a regional. The 8 year flow estimate at envoy will likely come down some as hiring opens up everywhere else.
From my prospective, it may be better to secure way into AA via the WO flow and apply to everyone you want to on the legacy/SWA/cargo list then go to a brand X contract regional that may lose its flying before you're competitive for who you want to work for (talk to the guys who went to AWAC in the last few years and had to leave and to start over at the bottom somewhere else to get forward career progression)or be locked out of a path to one of the "big 3" because 50-75% of AA new hire classes are flow through and most of the rest are transitioning fighter/heavy folks fresh off of active duty and your resume doesn't stand out from the 10K other regional pilots applying to them.