We've recently finished our fourth season with our 1975 8.0C, and routinely trailer it around Michigan.
Setup time runs 15 minutes to half an hour, and I have stepped the mast with the help of my wife or teenaged daughter nearly a hundred times. An aft cockpit boat takes a bit longer to rig, as the rear end of the mast needs some additional support provided.
Weighing over 8,000lbs with the trailer and gear, a main consideration is the tow vehicle, and slow speeds and good brakes are a must. Our three quarter ton '86 Suburban with 454V8, dedicated to the task, cost much less than half what 4 years of slip fees run, and greatly increase the number and variety of sailing venues. Being parked next to our deck, also makes repairs and reprovisioning much more convenient.
With the shoal keel, the boat draws only 30 inches, and if in doubt about a ramp, I'll wade in. If the water is waist deep, she'll float through, while launching requires a level area of chest deep water large enough to park the trailer's four wheels on, which, (thankfully) is provided at most ramps by power loading stinkpots.
In the event of a "hard" grounding, again I'll get into the water, attach a line to a halyard and heel the boat 25 degrees or more, while the first mate motors or kedges to deeper water.
We often draw skeptical comments, and incredulous stares, and on several occasions, onlookers have flatly stated that we just "can't launch that big boat here".
Being our 3rd sailboat, including an S2 7.0, we've worked our way up, learning as we go, and are happy to share our tricks with anyone that is interested.
While trailering a boat this size is not for everyone, we've found it much more satisfying, and no more expensive than other similar hobbies, such as snowmobiling, motorcycling, and camping with trailer or motorhome.
I believe Daryl has the answer for deeper draft boats, with his fifth wheel and strap, and sometime I'd like to witness a launching, and/or retreival like that.
Our 8.0C is shoal keeled, so we're only putting the dual tailpipes and a
couple inches of quarterpanel into the (fresh) water while launching.
I'm not sure our old suburban's tires and springs would take the additional weight that a tongue extension would add. And that "blub, blub, blub, blub, blub" sound, as the boat floats off, enhances the event, creating a true multi-media experience. Our EZ Loader trailer has rollers, which makes retrieval a (somewhat) drier operation for the truck. However, at this point, I'm wading again, this time to hand winch the boat onto the trailer.