I used to sail my Monty-17 to Catalina lots, and I was less well equipped than you sound to be. I circumnavigated Catalina once, and Santa Cruz Island once (both single-handed). Lots of single- and double-handed trips to Catalina. I sailed out of Marina Del Rey (where I dry-sailed it), or trailered it to Cabrillo Beach. I trailered to Oxnard for the trips to Santa Cruz Isl. I liked the Isthmus and other coves a lot better than Avalon.
I mostly anchored over there -- the boat is small enough to sneak inshore of the moorings in some areas. It really helps to have bow and stern anchors, and a dinghy of some kind (I had a little inflatable row boat), and a boom tent for the hot summer days.