one question for you. i haven't heard from Michael in a bit. i was wondering if you had any idea how i should set up the main sheet. my holiday 20 has the sheet routed no more complex than my dinghy. however, i am sure i will want mechanical advantage for the bigger sail. not sure how much, though, and i can't find anything cal 27 specific, on line. you always seem to have good info, so i am sure you might have a good suggestion.
Here's a simple 4:1 diagram from Harken
With good, low friction blocks I think this amount of advantage would be plenty for you.. with cheap blocks it will take more effort, but still doable, I'd think.
Is the traveler aft or fwd of the steering position? If it's aft I'd recommend running the business end of the mainsheet along the boom and drop it back down to a block ahead of the helm position. (imagine the drawing upside down, without the cleat shown at "B").With a tiller steered boat reaching behind to adjust the sheet is an awkward move. With the sheet forward it's a natural left hand for tiller, right for sheet on Stbd tack, vice versa on Port.
Ideally both traveler and sheet are forward in the cockpit (relative to the helmsman) but in any case control lines can be led to good positions with some thought. The advantage of an aft traveler is primarily a clear cockpit without shin bangers or other obstructions to moving around.
Our cockpit has a bridge deck traveler, but the sheet is on a snapshackle so at anchor we move it to the toerail to get it out of the way. No issue when not sailing, convenient and easy to use while under way....