My experience is limited to fin keel boats in the size range you are seeking. And it isn''t anything like towing a Capri!!
Although I have a launchable type trailer (20 foot tongue extension), I avoid this method if at all possible. Getting a 7,000# boat drafting over 4'', off or onto such a trailer is a chore. Secondly, these displacement similar boats have telephone pole type masts. Stepping 200# of +35'' spar requires rigging
assistance. Considering these items, it is something to be attempted seasonally, or, a cruise/outing duration of several weeks. I am not saying that any of these items can''t be done, it just takes time and the right gear!
Myself, and most others, I have talked with tow boats of this size with at least one ton pickups. For short trips around the town, I have used an SUV, but even these short distances, it feels uncomfortable. Additionally, these boats have over 8'' beams and require wide load permits, which is another hassle! Relatives have an Island Packet 28 shoal draft keel bought with the intention of trailering. So far in 15 years, a seasonal haulout/launch and two trips to the Gulf is it!!
Trailering, launching and reloading takes a lot of effort with this type of boat. Now, a newer water ballasted design changes a lot these considerations.