I've re-dislocated my toes so many times I don't care to count...lately, I've been taking a bit more time and 'sliding' my foot around the strap. Also, I found that if you can get your feet in the straps pre-planing (as you're increasing speed), it makes it easier, and less painful.
I still find that sometimes, the next day, when I look at my toes a couple of joints are bruised and swollen. The upside is, I know when rain is comin'