My rudder was in similar condition. After looking at the cost of paying for a new factory style rudder blade, or having someone repair it, or doing it myself.... I decided to eliminate the delamination problem, and get a better rudder design. So I got a ruddercraft kick-up.
When I ordered mine, they drilled holes for me so that if I wanted to order their mast crutch in the future, I could simply bolt it on.
I finally got my gudgeons installed and put the new kickup on last week. The instructions mention a "bungie loop" to be used when trailering. It's a mistake in the instructions, about something they no longer supply. Their current setup is a strap built into the custom Sunbrella rudder cover they sell, that also holds the rudder blade up during trailering.
As Don says, the gas strut holds the blade up or down, when in use, but also allows the rudder to kick up when it hits something. When trailering, there is a risk that the rudder blade will bounce down enough that the gas strut could move the blade into the down position. Hence the cover strap they have available.
They supplied a HDPE spacer block for use on either pintle pin. I have the CD retrofit upgraded 1/2" gudgeons, and the spacer block is too thick. I'll need to cut it down to fit.
I second the opinion of Ruddercraft, Catalina Direct. Both are small companies that know their stuff, and run their business like everyone else should. I haven't dealt with sailboatowners.com yet, (they are also RudderCraft Resellers), but I'm expecting they are the same.
Don: Eagerly waiting on the method they discussed with you.
EDIT: I need more coffee.. Just realized that the rudder portion of this thread is old. Oh well. Info is still valid.
Looking at these threads, most of us seem to work on the boats and not sail them.... LOL.
At least the rain makes it less painful. Nothing worse than a perfect sailing day spent with tools and varnish brushes.