David, assuming that no one has removed it (or modified it!) you can't tighten the CB bolt enough to clamp the CB in place. Two reasons (based on my experience) 1) there is (or should be!) a plastic bushing that the CB actually pivots on and it should be slightly longer than the CB is thick, the bolt tightens against this bushing and the CB pivots on the bushing. 2) The pivot bolt is not threaded for it's entire length, and you will run out of thread before tightening too far.
To fix a leak at the bolt, you can replace the 2 rubber washers/gaskets that seal both sides of the Cb bolt hole, these are available from D&R Marine (508) 644-3001
www.drmarine.com even so, it is recommended that you apply a bit of sealant between those gaskets and the side of the trunk to allow for any gaps.
I use a pair of socket wrenches (ratchets) to tighten my bolt, it is tight down there, but once you've done it a few times it isn't hard! I usually remove the CB from my boat every 3-4 years, to do a good cleaning of Cb and trunk, and get a good coat of antifoulant paint on as well. I keep my boat on a saltwater mooring all season (late May to Early October).
I'll add a few pics of my boat for clarity.
If you do contact D&R Marine, Rudy does have e-mail, but a phone call gets quicker service!
If it would help, I have created an expanded version of the original O'DAY DS II rigging guide, it contains more diagrams and info. cost is $10 to cover printing and postage, but should be worth it. Let me know If you would like a copy.
