If you are Hercules ...yes! Or you have set up some sort of rig to help you every time.
Some of these boats have drop keels so you can back the trailer into the launch area and get the boat into the water - again a job that really should be handled by two people.
I personally think that doing all this single
handed is a crazy idea - no offense. I single
handle most of the time and its enough work just getting myself launched or docked. I don't want to consider stepping a mast, setting sails, rigging etc. when I get to the dock. I just want to go sailing.
I have friends with a Macgregor and they do travel with their boat - but not often. Most of the time it sits in the marina ready to go sailing. If they are planning a week up north, they more often than not, just take the boat up and leave the mast at home and simply power boat
during those weeks. It can handle shallow water when the keel
is raised so they like to gunk hole.
This is not something I would want to do every weekend. Sailboats are a lot of work already so adding set-up every weekend adds 4-5 hours of work every weekend - set-up and take down.
there are a lot of great pocket cruisers that fit within the road width limits and would work for you. There was an issue of good old boat last year that featured some. Go to sail boat listings dot com and set your search for boats that fit within your specs and I bet you will find tons of deals.