Ummmm - I've done this before (for a still pic), but forgotten exactly how... (and I didn't keep any notes on how I did it, I was just playing around at the time..)

IIRC, it involved something like:
Got the skirt draped on zeroed figure, so it fell naturally (using real sim, not draping frames, draping frames are added BEFORE frame 1, so if they go wrong they can't be corrected).
Saved skirt at sensible-looking frame as .obj, exit & restart Poser. (This was to clear up memory, I didn't have much at the time.)
Reload (and zero) figure. Load the save (draped) skirt.
Go to approx frame 15, set up final pose for figure.
Return to frame 1, and contort the figure so that it can reach down and get the hands under the skirt. As close as possible. Don't allow anything to intersect - stretch arms, make any wierd pose, it doesn't matter - just get the hands under the hem without anything intersecting the cloth.
(I then ran the anim to make sure that the figure returned properly to the final pose.  Sometimes you get limbs going in silly directions - it's best to check first. If that happens, add a few key-frames to correct the situation).

Anyway, once all was set up (and I'd saved scene again, in case anything went wrong) I returned to frame 1, entered the cloth room, clothified the (new, draped) skirt, and constrained a couple of verts of the skirt near the centre of each of the palms.

Ran simulation. Worked OK.

IIRC, that is. To be more specific, I'd have to try it again...

Hope that helps,
Cheers,
Diolma