Launching: Mast & Trailer
MAST: The mast is heavy and I think requires 2 people to raise & Lower - One under the mast at the base tilted BACK to the stern - and another on the FORESTAY or other rope to help lift and or lower the tall mast. The boat should have come with a mast bracket for the cabin top and another for the cockpit rear - although if you have the stern rail option the rear crutch is not necessary. I have a taller wooden crutch I use which helps get the mast UP high enough for the front line man to get some leverage.
LAUNCH: The boat needs at least 2 feet of water to float off trailer. Also the TYPE of trailer makes a big difference. The majority of s23's I've seen have trailer that use bunks and support on the side - while my trailer has rollers - and makes it easier to get on or off the trailer. Also UNPLUG your lights. Be sure to have the trailer bearings checked and greased - and tires inflated to the correct pressure (it's a heavy boat!).
TRAILERING: The Trailer weight of boat, engine and trailer combined is easily 4000 lbs - not something a light truck or SUV can handle. That said I pulled mine out from a shallow lake ramp and drove it home over 300 miles w/ a Landrover LR2 SUV w/ a towing capacity of 3500 lbs. BUT IT IS BIG on the road - and is a maxi-trailerable boat in my opinion. Now I use a friends Ford 250 every season to launch and retrieve w/ a pretty steep local ramp.
MOTOR: The outboard also can NOT hang on the bracket during trailering w/ vehicle - the bouncing weight combined w/ speed can stress the transom, (even though it's beefy and can take a 9.9 100lb extra long shaft motor no problem at 5mph in the water.)
I keep my boat at a friends private dock (sailboats look great at a dock), and I think most folks only really trailer their S23s at the start & end of the season?
1977 North American Spirit 23