Some more info would help and things to also consider - warranty, hours, powerplant, options...etc. I was in a similar situation and asked the dealer the same thing when we were shopping. My budget fell into the 200 and 210 range, but both new boats. I LOVE the look of the SS, but went with the Frenzy because of the windshield and it still has the sporty look. We have a friend who had a boat with the low-profile windshield and warned us about the wind. With our small kids (all 3 under 9 years old) and my wife , we thought this was the better route for us. However, if it was just me...I would have DEFINITELY picked the SS.

I also liked the fact that the graphics are in the gel coat versus a decal for the Frenzy.
What will you be using the boat for most often? Cruising, watersports...etc.? For me, the majority of the time will be just for my wife and 3 small kids. We were also interested in wake boarding, tubing and skiing, so the Frenzy with side exhaust and tower was what we went with.
Initially, I wanted the bigger boat right away, but with our needs, the dealer actually thought I would be just as happy with the 200 and it's cheaper. His reason: only 2 inch gain in beam width, not much longer (19'8" vs 20'4"), a little more leg-room in back, but it's still the same bench seat and you really can't seat anymore...legally yes, but realistically no. There's no ladder up front in the 200, but that wasn't important to us. Ride wise, I didn't think there was too much of a difference. In my overall personal opinion, I didn't think there was much of a difference so I saved some extra $$$ and went with the 200. I think the big jump and where you will see real notable differences is the 200 vs 220.
Again, it depends on the powerplant, accessories, hours and condition of the 2007, but I am leaning towards new. The Frenzy edition was new for 2008 and changed again for 2009. I could be wrong, but I don't think the 2007 SS graphics are the same as 2008+ SS.
I hope that helps and good luck! Either way, I'm sure you'll love whatever boat you end up with.

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2008 Four Winns H200 Frenzy
MerCruiser 5.0 MPI/Alpha 260 hp