2.) Getting that boat to the EU is not impossible, but it will likely take a lot of money. It will need new rigging for sure, sails, unless they are very recent, and many other parts. To prepare that boat for a trans Atlantic crossing could take close to twice or three times the selling price depending on your standards. I also think you will need builders documents and Cape Dory has been out of business for a long time. They may be available, but make sure first. Make sure the standards it was built to will be accepted in the country you are exporting it to. I have heard that most EU countries are hard to bring boat into and likely going to be taxed quite high.
Seems like this is really not very feasible, as I can't imagine the boat would sell for much in the EU. The suggestion of a Folkboat is a good one. Likely many available, and likely sails at least as well if not better. Would have close to as much room below, though not as much as a CD 25D. Or a Contessa 26, or lots of others that will cost less than the upgrades needed for the crossing. I would look in England there seems to be a lot of small cruising boats along the lines of a CD that are quite affordable.