Largest trailerable sailboat
I think that you can tow pretty big boats such as the One Design 36''s if you have the right equipment, but towing larger boats can become a real hassle requiring special permits, etc. If you are only doing it once a year, this is not a big deal, but if you plan to lanch and haul with any regularity then I would think that a practical limit is somewhere down around 25 feet. If you bought a very light boat like a Laser 28 perhaps you might stretch that a little. Two big and knowledgeable people could step the mast on my Laser 28 without a crane but it was a little risky and was much easier with three people. I thought that the comparatively tall but rig on the Laser 28 was about as large as I would want to raise without a crane. I do not think of a Catalina 30 as being very practical as a trailerable boat.