I have been pulling a 24' Enclosed Trailer with 60" extended tongue (so I don't have the trailer and coach meet on sharp turns) for over 3 years with no issues. I have not been to CA with the trailer but many other states, just returned from Memphis yesterday.
I have only had to unhook the trailer twice in RV Parks that didn't have a space long enough for me to stay hooked. A little planning and it isn't an issue. Many times I drop someone off at the fast food stop and drive around the City block and wait on side street for my call to pick them up or park on Side Street and walk to establishment if it is a sit down.
I find most shopping centers have adequate parking and suitable restaurants when we eat on the road. We are not retired yet so we attempt to keep the travel time to a minimum from point A to B.
Good luck on your decision making.
2009 American Eagle 42'
Trailering HD Road Glide and Saab 9.3 or Cadillac Escalade ESV