I have thought about this more @inspiredgideon1. There will be no limit to winning. I want the best content to be rewarded. That being said, if someone is winning repeatedly they will be moved up in category.
Thanks for bringing that up about the skip days. More information will come out on this. But most likely 2 skip days in a row is the max you can do and remain in the challenge. 3 days off is too much momentum dropped and you will be removed from the active challenge.
Same thing will more than 7 (unless it is increased.) You will be removed from the active curation of the challenge.