I've been sailing one of two Catalina 36s out of Marina del Rey for the past 26 years. If you want to learn to singlehand, I'll loan you my friends.
I also actually singlehand often, mostly on weekdays when everyone is working. You will find that if there is any difficulty, it will be in docking/undocking. This is where a coastal fin keel boat like a Catalina excels. My boat handles like a really long car. Extremely predictable, relatively low windage and it stops on a dime (almost). I don't think I've touched the sides of my slip while docking in the last 20 years, even on windy days. Although I have a regular main, they can be had with a furling main which is really easy to handle. Just get yourself a reliable autopilot and you'll be set to go. The one thing I would mention about size, I moved up from a Catalina 30 (also a nice boat). The first thing I noticed was that when in choppy water, the 30 would bounce over it, but the 36 cuts through it providing a more stable platform. Aside from this, the 36 makes a great shoreside condo when you just want to hang out.