According to HD, you always have to replace gaskets anytime a part is R&R'd. Now personally IMO, that's just silly unless your talking about jug, head, rocker box, or cam/primary cover gaskets.
I just inspect it and replace it if damaged, otherwise reuse it.
I've had that breather on my scoot for about 15000 miles and have never needed to change the gaskets or those PITA o-rings. I did however, use sealer when Installed it.