Well, I can't help you with the working in Europe bit. As far as where to go, I suggest you read a guidebook that concentrates on the sights and scenery, and see what sounds interesting. There is culture and people in EVERY country, so you may as well pick one that has other things that interest you, as well.
Alternately, you can take the weather into account. Perhaps spend the colder months in the Mediterranean countries, and hang out in the rest of Europe during Spring, Summer and Fall.
Sounds like you guys have a heck of an adventure planned. Just remember that there will be plenty of little things that come up between now and then that will make you consider postponing the trip. DON'T! There are always nagging little reasons your doubts come up with, as a trip approaches. You have to be firm and disciplined, and forge through those...
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"Life is not measured in the number of breaths we take, but by the places that take our breath away..."