ahh, the Bend and the Cloth both want to do calculations on the points. The results can be nasty. If you were unrolling the cloth horizontally you could turn off the bend once it’s unrolled and let the cloth take over (or turn cloth on at that point) and it would drop. But since you are unrolling vertically and the cloth is meant to hit the floor, you can’t turn off the bend and let the cloth take over because once you turn off the bend the cloth reverts to straight in a single frame and the cloth can’t deal with that.
The only solution I see (someone else may know something better) is to use the bend to roll the cloth, do a Current State to Object to freeze that. Then scale inwards with a soft selection to get the cloth not touching itself in the roll, then apply cloth tags to that with Self Collision turned on and let the cloth engine unroll it. Like this but if you need to have the roll be smooth like if it was being done with a bend deformer it would need something different.