Could you describe in more detail which effect you want to achieve? When aiming just for the skirt to be raised, I would go for the following:

1. Use timeline with 60 as upper value 1a. at 0 have the figure in a slightly modified bas position, with arms to the sides and the feet close to each other 1b. have the cylinder below of the feet
2. at 30 put the cylinder upwards a bit higher than the position needed to move the skirt up as far as you want 2a. don't change anything of the female's position - yet
3. at 60 move the cylinder down again and set the female's legs into the position you want them to be 3b. move the arms into the needed position after the simulation

I have not tried it (but I think I will...) but doing it this way those problematic "double collisions" should be avoided.

Another option would be doing the simulation with the figure staying in the basic position - with feet close to each other - and using only primitives as replacements for those parts of her body, that are supposed to interact with the skirt and moving her limbs into the correct positions after (!) the simulation. In my - limitied - experience, dForce works way better when only primitives are involved.