Thanks. I gues there's no easy way out, or else everybody would be doing it.
Andy,
I'm not saying that it can't be done. I really don't know all that much about the O'Day 20 and how the reefing would work if you were able to do it from the cockpit. The O'Day 272 is set up with everything handy from the cockpit including two sets of reefing points, a mainsail jack line, topping lift, and halyards. I can only speak for my O'Day 222 which has Z-Spar internal halyards and control lines going through the boom. The boom's goose neck is fixed to the mast and there is no tack down haul. When I want to reef my mainsail, I need to let one sail slide out of the mast track first. It's quite possible that you may need to do this too, I really don't know but I believe that the O'Day 272 has the Mainsail jackline for the purpose of throwing slack into the bottom portion of the sail luff for this reason. Failure to remove the last sail slide from my mast track while reefing will put excess strain on that sail slide and cause binding when I go to raise the sail. The sail slide will eventually break too.
I'm kind of a nut when it comes to walking on my boat. I've been doing it for years and I've grown quite used to it. Nothing seems to bother me when I'm on that boat. A sheet gets snagged sometimes and I have to walk to the mast to clear it. A good friend of mine gave me a whisker pole off his Hunter 27 and in order to set it up, I need to set my Autohelm and walk to the bow and pole out my Gennie while she's sailing on a run. If I should fall overboard, I don't think my dog Penny is going to be much help. She hasn't quite mastered the MOB maneuver as of yet. So the answer is, be careful, don't take any chances, and avoid falling overboard by using one hand for the ship and one hand for yourself. There's one other thing that I'd like to mention. Sails will last a long time if you take good care of them by covering them whenever you stop to anchor for any short length of time, be it stopping at an island for 20 minutes or a half hour to take the dog over in the dinghy to curb him or having your lunch break. The more you climb around your boat putting on and taking off the sail cover, the more it becomes automatic and you get used to it. Whenever I stop out on the bay at my favorite anchorages, I cover the mainsail and install my polytarp over the boom. When I get back to the boat from curbing the dog, the cabin is nice and cool.