So from what I've been able to tell, AEW gets around the critique of calling it's wrestlers independent contractors by doing what the WWE is supposed to do (allowing outside bookings, etc.), while also giving its long-term talent jobs on the side to justify giving them benefits. Do you think this is a good workaround, or is this still stiffing the talent in some way?

I think it's a good compromise to let people who aren't top-top guys take outside bookings, especially since they don't run house shows.  Really, I bet if the guys bloating up WWE's roster like Luke Harper were allowed to go use their name to work some indies and stay busy in between appearances every six months, they'd be a lot happier.  Now, this does get into the major issue of "What if they get hurt working outside shows", and admittedly I have no easy answer to that one.