Re: Thinking about upgrading...
"Lots of choices, but if you buy basic strong construction over "dock side condo" styling and quality, you will always be happier in the long run".
I really agree with this sentiment as you consider both boats. How the boats have been maintained and what "upgrades" have or have not been done (autopilot, chartplotter, newer sails, etc) also should influence the decision.
Everyone has different preferences about cabin size and layout. We are very happy with our "move-up" boat, '97 Caliber 35 LRC... traditional layout, very solid construction with quality portholes/hatches/winches etc and loads of storage for the longer cruises we can now do. Sailing characteristics and "seakindly" motion matter too... should be fun to sail! Thinking about how you will actually be using the boat (and where) should dictate what is on your "must-have" list. For example, sailing in warmer climates means ventilation down below is important. I am the "Admiral" in our case (hate that term), but I would advise other wives/spouses not to get infatuated with the dock-side condo aspect of a boat... a well-found sailing vessel doesn't need fake flowers on the saloon table!!
Good luck, and enjoy the search!