Flint, your list is amazingly thorough. Well done, sir!
Based on his ties to Cap and Barnes, I don't see Falcon joining Simon.
Simon would have ties to US Agent, the second Spider-Woman, and Living Lightning from his WCA days, but US Agent is too involved in his post as the Thunderbolts warden to get involved in Avenger business (incidentally, he's an even bigger bad ass in a wheelchair!); Spider-Woman is doing Spider Island stuff; and last I understood, Living Lightning was still in college (which is why he left the Avengers West in the first place).
Stingray might be a surprise fit. . .not much has been done with the character since The Initiative ended.
Gilgamesh (the Forgotten One) would be a great fit, since he's had a pretty miserable run as an Avenger.
I can see Swordsman, Yellowjacket and Deathcry running into Simon post Chaos War, and using a second lease on life to try to "undo" whatever damage Simon believes the Avengers are doing.
But this brings me to a concern I have with the direction Simon is going: he's a second-rate inventor/Hollywood stuntman/invulnerable powerhouse, not an ideologue who gathers an army to make a stand against former teammates. I'm concerned that Bendis is taking this character into a direction that doesn't make sense, given all we've seen him do.
Living Lightning: Isn't he a Ranger now, too?
Stingray--Man....that would be a cursed blessing, I tell ya. Love walt, and I'd love to see him get some face time...but I don't think this concept (from what I've heard thus far) fits him.
I dunno about the fit. It really depends on how it's portrayed. Simon's been shown as capable enough at making a solid argument at times. (ie: Not giving Vision his engrams again, or participating in the anti-Supreme Intelligence regime). And, from what he's been shown doing/saying in the pages of the book itself it makes a little sense. If they go too over the top though, I agree, it'd be bad.