Like Timbo, I keep as much rigged as I can IF the trailering is relatively short, say under six hours, and I am going to rig the boat again soon. Otherwise I remove as much as I can. It has to be an unusual situation to remove the diamond wires. There is no reason to remove them normally. A good way to contain everything quickly and securely is to use plastic stretch wrap on a handle which you can buy now at most big box stores and hardware stores. It comes in several widths - I like the 6" width for all-purpose use. One roll lasts a long time even when you use a lot to pack up and it is fairly inexpensive.

If you trailer frequently then it is worth the time to develop cradles, jigs, devices, etc. that make de-rigging and trailering simpler, more secure, and quicker. For example the Taipan was usually sold with a trailer set-up that included a sail box and a receiver/stop (Y shaped) that the dolphin striker slid into and held the boat securely sideways, and prevented forward, and even backwards movement when latched. I have seen that idea developed so that the whole light weight rig can be moved off the trailer with its own wheels and moved around to free up the trailer for other uses as needed while the boat is still secured. It just depends on your handiness and whether or not it makes sense for the way you use your boat and trailer.