i haven't tried seymour yet but i found grouse to be much easier than cypress. maybe because the ride to get to the base of cypress is already hard-ish. i hear the S2S is
very windy so maybe try something like what bcrdukes suggested and ride somewhere you can work against headwinds. I'd recommend a Richmond loop around the whole city for that but it's super flat...bleh! no hills to 'tack
@Kilinim - I'd consider doing the ride again but 2.5k was honestly a huge commitment that I don't think I could do once more. had a hard enough time milking my networks for donations last year

Great great ride though.