I subscribe to the Norse fatalistic view that the weather will be what it will be.
If I was an out-of-towner I'd probably head to Chatham - either the Causeway or Hardings Beach - the beach is the easier launch so if you are new to getting your stuff from the truck to the sand you'll probably find that more relaxing - its also an easier paddle to N. Monomoy. The Causeway you can either launch in the Tub or Stage - but you will have to carry your yak a fair distance which can be a problem especially if have a peddle boat - and especially if you got the peddles because your arms are weak. Its about 500' to the tub maybe double that to Stage.
If the wind is very bad but you still want to yak it, Bass river at High bank Rd or Herring River at 28 both have nice launches.
Another option is Pleasant Bay - it used to be great but last year the seals really set up in it and some moron - most likely a New Yorker - started feeding them. So minutes after paddling out you would be mobbed by 30-50 800lb animals that were acting like Golden retrievers - I doubt they were dangerous but definitely uncomfortable and not the best way to fish. Last year the further from Chatham the seal deal was more manageable. But now with the new cut established and the Chatham harbor silting in - I don't know.
There are other launches but Al Gore will be a 150# libertarian before I give those to anyone.