Not too diffacult
We have trailered our C27 for the last 7 years, including trips that cover several thousand miles. With a well designed trailer and an adequate tow vehicle (rated to tow at least 9000 lbs) maintaining normal highway speeds is not unusual. Launch or recovery (from the trailer without a crane or travel lift) takes about an hour with the right equipment available. The mast stepping/unstepping is probably the most critical step, we've used cranes, mast poles, and travel-lifts, as long as the process is well thought out and you have control of the mast throughout it should become routine after several evolutions. At one time the plans for a wood bi-pod arrangement were available on the net. It looked like an ideal system that was easy to use and inexpensive, I suggest researching it further. Our trailer was designed with the assistance of several structural engineers, it is as light as possible (without going to exotic materials) and strong enough to hold a C30. The combined weight of boat and trailer sits at about 9000lbs, this I think, is the minimum weight you should plan on. Our tow vehicle is a Chev 3500 (dually) with diesel engine, I would not recommend anything less than a 3/4 ton truck with towing package.Best of luckEG