[jcwhite]

Hmmm, it looks to me like it would be a lot harder to shift the C&C overland, is that fair to say? However, it also looks like it would be a much better boat to run up the outside with, once I get to that stage of sailing. Are there any major differences in build quality between C&C and San Juan?

As long as it's predictable and I can work with it I'm not too concerned about getting 'a lot more boat'. If they're too squirrely I'd definitely start to get nervous.