been there, done that
about the whipping... i know you said you used the 1" webbing w/ cinch buckles, but how was your support system connected to the ends of the hammock?
i use a larks head which tightens more as it's weighted & it sometimes doesn't even travel as far as the whipping because it's gripping so hard.
i use a larks head on cord to connect the hammock to the ring buckles now, but i used to attach the webbing to the hammock the same way ...no problem.
and about gathering the hammock ends to be whipped... i think cannibal is right... at least that's the way i do it... i pull the corners about 2 or 3" out before whipping rather than pulling the middle out.