Originally Posted by wumhenry
..The fairleads are on a track on the toerail. I don't see any evidence that they were ever located inboard.
Fitrst, trimming the jib to the toerail automatically hits you for something, say 5-8 degrees versus use of an inboard track. You might see if other 29.9s have inboard tracks. If you decide to install one, get the location measurements from another boat, or someone on a Bristol list may be able to provide.
Secondly, how close do you trim the jib and in particular the main? A common guideline for trimming a jib with an inboard track is 2 inches off the spreader tip, I'm not sure how that translates for toerail trim- never trimmed a closehauled jib to a toerail in 30 years,,,. The main needs to be trimmed to just before the leech telltails break, the top one should be lifting. Mainsail trim is a bit of an art, you need to use the traveller (if you don't have one, thats another couple of degrees you lose) and sheet together, a lengthy subject you should find in available tuning guides.
If your rigging is holding the mast straight, it ain't part of your problem. You can judge that by whether there's much slack in the leeward rigging when closehauled in a moderate breeze. If there is noticable slack, tighten 'em up. Theres no way tired rigging should contribute to poor performance (up until it drops the mast on you.)
If I were you, I'd try to get an expereinced 29.9 owner to go out with you once.