My holdups on the H33 are:
- Is the aft bunk full size/length? I'm not tall, but don't want to scrunch up.
- I hear lots of complaints about the 'dorm fridge'
- Smaller fresh water and fuel tanks (VS the H356)
- Smaller cockpit size (It appears to be, but I haven't been on both side by side to compare)
- Smaller interior volume (although, I have yet to step on board one, so it may not even be an issue)
I'm 6'-2, aft bunk is more than comfortable. The hatch overhead is great for letting in light and air flow, we rarely are too hot sleeping. Only drawback is disrupting the partner in the middle of the night.
Beer fridge is same size I've seen on all other size boats, small, but we survive for a week onboard. We also turn down (up) the freezer to fridge temp to use for some items at times, but still draws a lot of power.
Fresh water tank is huge, fuel is not bad, holding tank is usually our limitation for how long we stay out, 4-5 days, sometimes push to 6 and full.
Cockpit is good for 2, and gets crowded with 4-6. Biggest issue I have is getting to the Main sheet or to the main furling lines with more than the 2 of us on board.
We were at the Toronto Boat show this past weekend and friends with us and all commented that our boat felt more spacious inside than the bigger boats we were looking at ( Bene & Jenneau )
Overall, we're more than happy with the boat and has been great for the past 8 seasons. Looking back, it was our first boat so bought based on what I was used to handling ( CS33 ) so went that size. Now, I wish we had gone bigger, only because I could have handled a bigger boat and the extra space everywhere would have been nice. If we'd bought the 36, I'm sure we'd be content right now ( yes Nick you're correct

) but now we're looking either 38 or 41 in the '04 - '08 range.
Downside I've seen on the 356 is not having the jib sheets back to the helm, which would be a problem for me with several people on board.
Also, I wouldn't be too worried about the earlier models ( 04 - on ) in this area ( Great Lakes) It will be more dependent on how much the boat has been used and/or taken care of vs. newer. A well taken care of older boat will be better than a newer neglected boat.