I'm not sure if I'm going to be able to explain this well enough, but I'll give it a shot.
While I don't mind creases per se, I've been playing around with different methods and what I've come up with that works pretty well is actually two different things at different points in the process. The first is not exactly perfect, but over the various flips and redresses, it seems to work pretty well.
What I have to do is get the curds into the mold, put on the follower and then start pulling up on the cheesecloth bit by bit around the sides while I'm also pushing down on the follower. I sort of shift the cheesecloth around a little bit while pulling up on it, so that while there are still creases, most of them are NOT near the bottom where the cheese will end up getting pressed to. Hard to do neatly with the initial curds, but works better after the first redress when I pull off Trick #2.
When it's time to redress, I get the cheese out of the mold, pull off the cheesecloth and then center the damp cheesecloth OVER the mold - but I don't actually push it down. Then I stick the flipped cheese on top and start pushing down and let the cheese itself work most of the creases out. I still do the follower/push/manipulate-the-cheesecloth thing afterward, but I get a better start on that, beginning with the first redress, since I've basically let the cheese do most of the uncreasing for me. I just have to be careful not to let the cheesecloth get caught and ripped in the "half-holes" around the top of the mold (I'm mostly using the stainless one from NE Cheesemaking).
Only weird part to all that is that at the first redress I usually have to also sort of squoosh the vaguely-cheese-shaped cylinder around the sides to get it to fit into the mold again that first time - no matter how quick I am on that redress, it will usually slump a bit on me, so I just have to bully it back into shape.
I still get a few creases here and there, but very minimal. Especially when I flip and redress an extra time or two from whatever the recipe technically calls for.