Re: Reefing set-up for Contessa
Harken and Ronstan have various single and double line reefing system diagrams in their technical information. On my Vega, which sounds pretty much like your Contessa, I've actually found I like the simplicity of the system. My previous boat, although smaller, I had modified with all the sails controls coming back to the cockpit but really found it a waste of time on such a small boat, even when single handing.
The big problem with the Vega is it used a roller reefing boom, now hopelessly out of favour in the type of configuration used. Consequently it is no longer used which leaves no original reefing system. My simplified reefing consists of using an "S" hook at the front of the boom that attaches permanently to the gooseneck and hooks into the selected reefing cringle at the tack. At the rear of the boom, I use a piece of rope (the same piece of rope I use to tie the boom off to the backstay to stop it from swinging when moored) to pull the clew downwards and backwards and tie it off at the end of the boom. There is a way to wrap the line around the clew's reefing cringle so that it pulls down as well as out when tensioned. As for tensioning, I had no problems with simply hand tensioning the clew reefing line (without the sail filled, of course), but thought I could improve on it, even though the boat still points well when reefed which is really all the sail shape I care about. I installed a turnbuckle to allow me to mechanically tension the reefing line at the clew, but found that all it really did was put too much tension on the foot of the sail and caused the sail slugs to pop free from the lower part of the luff. My solution will be to rig up a cunningham for my sail which I think will solve the tensioning problems, and will be easy to implement and use.
From your description, the forward in-boom outhaul might actually be a cunningham control?