Thanks for the advice.
The market on used isn't looking great to me right now. I can buy a 3 year old boat for $2k/$3k (15-20%) less than new at best which isn't a great savings in my book. The question we're asking is: Settle for what we can find used or buy what we want and then if we decide we don't like it sell it in a few years and lose $5k if that. I think we've pretty much settled on new. We've looked at older used ones and they are just beat up and newer used ones are expensive in my opinion.
I'll clean the hull myself. I grew up diving and scrubbing my parent's boats and when racing we would scrub the bottoms on the sailboats monthly.
That said I'm thinking that we'll probably end up getting a trailer sometime in the summer. If and only if the current Subaru station wagon can pull it (tounge weight limit is 300lbs). The other issue is storing it because Meaghan doesn't want it sitting in the yard.