Wow Everyone - thanks for the feedback!
We traveled 500+ miles in two days and looked at 4 boats. The C&C did look to be in pretty good condition for its age, but there were a number of questions about it that made us turn away. I think it's a great bargain for someone else.
The Catalina 320 in Manitowoc looks like the winner. Now is the part that I'm not good at, the negotiations. Fortunately my wife is really good at that. There are just a few little things we have to work out.
@Scott T-Bird you are right. Ultimately for what we plan to use it for, there is no comparing the two.
What I HAVE noticed though, is that a lot of the boats I've looked at that are 80's boats and $20k, someone has done a lot of the work and the investment. New standing rigging (by the way on the Great Lakes standing rigging lasts damn near forever), new sails, new cushions, dodger, Bimini, re-bedded EVERYTHING, rebuilt engine, new or updated plumbing or electrical. Sometimes the 90's boats have not been touched. Thirty year old sails, 30 year old cabin cushions, original everything, nope the fridge doesn't work, neither does the cooktop, yup there's a lot of mold down there, we mostly try not to look at it - it hasn't really been sailed in years - that will be $50k please.
So in some cases (from my experience) that $25K really IS the sail away price, the $45k is the down payment.
Things don't work as well when they age, something is going to break no matter what, but 1995 sounds better to me than 1981.
My plan is to get a slip in the Manitowoc marina for a week so that we could get some lessons on the new boat and the systems before we start the delivery cruise. A logical route for the delivery cruise would be crossing Lake Michigan from Manitowoc to Manistee on day one. I'm 90% super excited about that, 10% terrified.
Terrified might be too strong . . . check the forecast and pick your days and all that. Still - I've seen Lake Michigan when it's angry. It can turn from Bruce Banner to the Incredible Hulk in a pretty short amount of time.
Let's just say there's a healthy respect.
Every time I sail over a Great Lakes shipwreck I remind myself that the captain of that ship was a professional.