I have epoxied in stainless steel Helicoils --not in a kayak, but same principle.

Spreads the load over a bigger threaded area. Just make sure the bolt threads are lightly lubed, but not so much as to interfere with bonding. 

Thanks Garland. I was thinking along the same lines by applying some petroleum jelly to the bolt threads, then screwing the whole thing into the epoxy coated hole. But then again, maybe just use silicone, rather than epoxy. 

Never on a wooden boat, but i usually use threaded inserts for bolt on guitar necks.  Brass is pretty delicate, stainless steel is a lot more expensive, but a lot more rugged.  If you are are thread challanced at all, go with the SS, it means not having to drill out inserts in the future.  No problem with brass screws in SS inserts, so it does not really change the asthetics.

And ick on heilicoils, solid inserts are worlds better, I do use coils in a pinch, but never by choice.

I use brass inserts on items that will be removed for service or maintenance. Bed them in epoxy or use the drill-fill drill method. It makes for a nice clean install.

I have used the brass inserts on cabinetry and have broken a few of the slotted ones in the process(in hardwood), so started screwing them in with a bolt rather than the slots. But I like the flanged kind with hex drive but have only found them in zinc alloy(checked MSC, McMaster Carr, Granger). So came across these today that look promising. They don't screw in, but drive in. They look promising. 

http://catalog.yardleyproducts.com/printitem/sharp-sert-flanged/sharp-sert-insert-us-threads-2/1024sf12-12br-2?&plpver=10&assetid=&origin=&by=&filter=

dehager, 

I've seen your Mill Creek rudder install photos. Very neat!

well now I've found, again from yardley, self-tapping inserts with no slot and almost 1/8 in longer (the flanged ones are .375 in long versus .469 for the non-flanged for the 10-24 size). They might work better since they will bite more into the shear clamp. I might order some of both and try them out. 

Yes..you can try both but make sure that the both have a same thichness and same in length.

Buy kitchen cabinets

Just lovely,  I usually use the commercially made stainless studs, I will have to think about going your route because they are lovely.

I am looking for a discussion on deck recesses.  In that regard I stumbled on surfboard leash plugs.  If they were al little larger they would be perfect.  I did find leash plugs with a 1-5/8" OD which would be fine (I think), but they were a site in Australia and I could not connect with them.  I have ordered  a bunch, but they are only a 1" OD.  Unless i can figure something out they are too small.  However, If you are looking for recesses for your deck rigging, explore this avenue. 

IMO that Seems like a whole lot of trouble when a wood screw would work just fine.  last week I was working on a mahogany runabout built in 1961 and only ran across a few worn out screw holes and that problem is very easy to fix. 

For a spare paddle, I made a Greenland storm paddle.  It is attached with using a small bungee loop through the stern lift handle hole of my Shearwater, and the other end sits under the rear deck bungees.  Simple, no holes or hardware needed, and it works great.

"....only ran across a few worn our screw holes and that problem is very easy to fix".  

Agreed. But my original post was about reconfiguring deck rigging. I doubt the boat you were working on was previously abused with multiple reconfigurations of rigging. And threaded inserts are really no more hassle than a basic  wood screw. Dave