Welcome to the emergency room. It really is an illness, and most everyone here is infected by it. After you get the cure for this one (that means pouring money into a hole in the water) you get the next stage which is called "two-foot-itis". Thousands of dollars later you are still infected, but happy.
First, determine if you really want to sail or be a stink-potter. You are in an area with a lot of sailing schools, so take a class in a larger boat to see if you and your admiral really love it, like it a little, or hate it. ASA 101/103 is taught usually on a 30' yacht, you learn a lot, can usually stay on board or not, and over four days you usually get to experience some different weather. Invest $1200-1500 to find out if both ofyou, or one of you, like it before you invest that $60,000 in something that can become a guest cottage,with a lot of upkeep, on the end of your dock.
The reason that there are so many good deals out there right now is that we are definitely in a buyers market. Fine if you are a buyer, but in 6 months if you become a seller you are on the wrong end of the deal. I believe that the average time on the market is over a year at the moment.
That 4'6" on the end of your dock limits you considerably. That Catalina 30 with a wing draws 4'3" BEFORE you load her. Don't know about the channel to the bay, but its depth will also restrict you.
From experience, you are making a very difficult decision. I have been around water all my life, mostly small sailboats and 18-24' runabouts. Five years ago I got the bug for a larger sailboat. Did the ASA 101/103 on a 30' followed by the 104/105 on a 37', and found that I loved it. Did both of these without my wife as she was really not interested. Knew that if I ended up buying the boat that I would be single handing the boat, or with friends, more than with my wife. She would do some day sails and maybe one week long trip a year depending on the weather. She gets motion sickness and has not found a cure for rough weather even though she has tried most everything from prescription to pet cures.
Bought a 34' anyway because I love it and life is short. Single hand most of the time and with my wife when the winds and waves are realistic for her. Have a few friends that love to sail, and do a couple of week long trips a year with them. Long trips with my wife will be me sailing and her driving to a marina somewhere to meet me. Caught out too many times on longer transits when seasickness has caught her in even benign conditions.