Catalina 27 or 30
The Catalina 27 is a "starter boat" and few keep them long. But there is a big difference in price. If you have the money for the 30 then buy it as the 27 will fail to do the job of comfortable cruising.
I don''t know where someone got the idea that a tiller is better for single handing. A tiller with a AP and a wheel without sure.