catalina 34 Mark II or catalina 350
I moved up from a Catalina 22 to a Catalina 350. First couple of times out on the 350 felt like the boat was very "big" but over time it''s gotten "smaller" in terms of ease and familiarity of handling it.
Prior to my shakedown cruise, my 350 was docked in line with other new Catalinas and was in front of a Catalina 36. The 350 certainly looked much larger than the 36; the 350 does have more freeboard, which contributes to this perception.
I have a number of features on my 350 that greatly facilitate single-handing: autopilot, electric halyard winch, furling genoa, all controls led to cockpit. If you get no other option on a boat, get the autopilot.