Great Questions, Paul
The maxi-trailerable boats that you will likely find on the market will be something like the Hunter 240 or Catalina 250, which use a combination of retractable swing-keel to make it ramp-launchable (see George's pic of the Hunter 240 up on the beach with the keel retracted), and water ballast tanks, filled upon launching for stability, drained upon recovering to the trailer) to make it lighter on the trailer and possible to pull almost as easily as the Venture. These maximized trailerable boats can do all the coastal cruising you want, but cannot wander far from shore. And offshore capability is not something you really need right now anyway; you just threw that in as an eventuality in the future. That will be a different boat.Judging from your post, what you need right now is a boat with enough room and creature comforts to sell the family on daysailing/coastal cruising, but is small enough to pull behind you up and down the West Coast.A larger, non-trailerable boat is pretty much tied to a local cruising ground, unless hoisted on the back of a lowbed trailer and hauled down the highway at an obscene price. As for delivering the boat over the water: I have a 30-foot Catalina, and I certainly don't want to go through the ordeal of motor-sailing it against wind and current along a lot of barren coastline from say, Santa Barbara to Seattle, and then to Vancouver.But water-ballasted trailerable boats like the ones mentioned above can go with you all up and down the coast without the need for a semi-truck. They don't need to be hauled out every couple of years for bottom paint (if you're going to splash it for the whole summer in a slip/on a mooring, a coat of ablative bottom paint applied while on the trailer (blocks and hydraulic jacks will let you paint under the trailer skids). If you're going to "dry sail" the boat (haul it out after each excursion, outta be able to stay in the water a week or so without too much bottom cleaning on the trailer later), no bottom paint is likely to be necessary.With as little bias as I can let slip in, the MacGreggor is a hybrid sailboat/powerboat: trailerable, lots of interior room, very large outboard engine that will let it zoom over the water; but the hull and rigging is light, and in my opinion, should only be sailed in protected bays and inland waters, although they can be taken to the Channel Islands. Promising to give "everything, affordably" it gives nothing well. But they have their enthusiasts.Water-ballasted, swing-keeled Hunter 240/Catalina 250: good calls for where you are right now.Fair Winds,JeffP.S.— The Category A, Category B, etc. ratings designate supposed theoretical capability: A for off-shore, and then descending. They are used largely for insurance purposes (and to fuel arguments on sailing bulletin boards), but in your case, they really won't come into consideration.