Ummm...Mr Hartley, sir? How did you end up with that mess?
I think you are overcomplicating life a little bit.
The boom on an endeavour 24 is not much longer then yours and we just used two plastic Whitworths fairleads per rope to bridge the length and keep the rope form sagging into a garrot over the cockpit.
We have two reefing points in the main and thus a reefing line runs on the port and one on the starboard side of the boom. For boats as small as ours single line reefing is fine, if it is set up right.
Send me an email at akharnam(at)optushome.com.au and I will send you some pics and MS Paint diagrams of how we set up the mainsail reefing system we have just done.
On a totally different note, since you are a denizen of Corio Bay...Could I get you to take a peek around and see if there is a sail yacht for sale in the 25-28foot range for someone with a hull budget of around $12K. A friend is on the hunt for one and internet listings are looking very paltry right now. I have alsways found the best way is just seeing what is pinned on the noticeboards of the clubhouse...So if you happen to be in the neibourhood...