My point was that cowboy rescues don't work in real wind and waves. Paddle float rescues don't either.

You keep saying that......
;-)
Not the way I'd do it (paddle is leashed to the boat, and he goes over the stern) but here's another cowboy:
http://www.youtube.com/watch?v=eCC-oX-OsWg

Well, we really need to define 'real wind and waves' here.

There may be some particular conditions where a paddler who failed in (several attempts at?) rolling and had to wet-exit, could then successfully do a re-enter and roll, but couldn't do a paddle-float or cowboy self-rescue. What exactly are those conditions?

And, in those conditions, how exactly does the paddler pump out the boat (standard 2-armed paddler) and stabilize the boat without using a rafted-up buddy or paddle float for stability?

Of course (since it's usually harder than a roll), the re-entry and roll is a technique strictly for competent rollers. And if you have a combat roll, when would you need it? (Pool trick?)

The paddlefloat re-entry and roll is pretty easy for most beginners. Of course, once you do that, you don't have the advantage of the stabilizing float attached to the rigging aft the cockpit (which you have in the standard paddlefloat self-rescue) , so pumping out becomes a major issue.

The anti-paddlefloat mantra is associated in my mind with the BCU and Brit boats - virtually none of which have decent rigging aft the cockpit for a paddlefloat stabilizer/rescue. There's lots of 'history' to that- going back to Derek Hutchinson vs Matt Broze, UK vs USA, etc.