I have a Catalina 30 and I would strongly recommend it for what you are looking to do. I was also a single parent in the military, Navy (several years ago). There was a suggestion that you could go smaller to save some money. Well the Slip will be one of your biggest concerns but at $2.50 a foot the difference from say 27 footer to a 30 is only $7.50 a month not much savings for the comfort. You will find that the interior of the 30 seems about twice as big as the 27. The 30 would be very comfortable even if your daughters are all grown up. I know three people that live on their C30's so there should be plenty of room to have fun. I have never gone out alone (I have lots of friends that are always available to go sailing) but I know several people that single hand their Catalina 30’s. We have one guy in out club that races his 1977 Catalina 30 single handed and he is normal very close to the front and normally beats bigger boats. The Catalina 30 is one of the most popular boats ever made. Somewhere close to 6,500 of them built and most of them including hull #1 is still sailing. This gives you a lot of sources for parts and experienced sailors to give advice and recommendations. I hope my two cents helps.
$2.50 A FOOT IN SAN DIEGO ??? I will take it. Were are you?