neither is Omni easy to get on with. He absolutely can apply off the street to legacies along with 14,000 other non-military pilots. He already has a legacy job in his back pocket with no interview.

if he is under 50 he will make more money at AA. He will have trip variety at AA. He will have no whipsawing at AA, whereas ATSG owns three very similar airlines. Omni & Kalitta are small operations compared to AA. He’ll have better retirement at AA. He’ll have more fleet types available at AA. Unless he’s over 50 or absolutely can not do 3 years as an Envoy CA making $100k+ then he should stay where he is. I’d say the exact same if it were Jetblue, Spirit, Frontier unless he lived in base. He’s so close to a top tier legacy job that he shouldn’t throw that away.

I’ve done both. I’ve been less than three years from flow, and I’m at Omni. If I had the choice I’d wait the 2.5 years and go to AA. Omni is a great job, and a solid career in its own right..... but it’s not a legacy. The grass is not always greener.

That all said, for a new hire... I’d never choose an AAG regional. The flow will be worthless insurance you’ll never use as street hiring will be ferocious. Flow just won’t be needed.
So, could he go do Omni & K4 for a few years and then street apply, yes. But he’d be applying for a job he technically already has. He’ll make as much as an ENY CA as an OMNI/K4 FO for the time period it takes him to flow.