Jonathan, with some practice, you should be able to get it down to 15 minutes. When Rick and I were racing our Hobie 18 every weekend, we took 15 minutes from trailer to fully rigged and ready to sail; and it took us 15 minutes to be ready for the road again. And there was more to do with the Hobie 18 than with your Prindle 16.

Establish a routine and follow the same routine every time -- do specific things in a specific order.

If two people are working on it, each should have their own part of rigging/de-rigging they are responsible for -- like one puts on the main and the other puts on the jib.

Figure out a quick and easy tie-down system so you are not always hogtieing everything all different ways every time.

We never took anything off for trailering (except the daggerboards, of course). The only stay that was detached was the forestay at the lower end where it attaches to the bridle.

Lots of other people like to totally strip their boat down for trailering, but we're not organized enough to keep track of all the parts and put them back on exactly the way they were before.