Merry Christmas and happy anniversary!
I think you need to go for the Win , Win scenario. By all means go on the cruise with your sweetie. This is not even on the table, first mate comes first, no question. The add says "Will deliver for gas money."
You call up the owner and see if it has a keel, etc first. Then set up a delivery date after you return from the trip.
Put the C-20 up for sail at a break even to a small profit range. Owe silly me I said the "P" word in reference to a boat. Some times I just crack myself up.
Get a start of Cleaning and fixing her up for the Spring sailing season.
Owe, keep your current trailer for the new boat.
Also look at that new boat, it is gorgeous. it looks just like my boat and I have a darn fine looking boat if I do say so myself. It's a Chrysler you know.
Thanks
Alan