From the point of view of acclimating to a different culture, it really depends on your personality and where you live. I didn't have any problem at all, but every once in a while I meet someone stationed here who can't wait to go back home. Most of the other Americans living here that I talk to love it though.
However, you can't just pick up, move to another country and look for a job; you need to have the job lined up first and apply for a visa. For example, it would be illegal for you to either live in or work in the countries in Europe (or elsewhere) without obtaining a visa that allows you to live and work here before you come. Right now, the economy is not good and there are not many jobs available; hopefully, it will be much better by the time you're ready to move. EU citizens have the right to live and work freely within the EU, others cannot automatically live and work here.
My direct experience is with Italy where I've been living for the past 13 years; other countries here in Europe will have similar rules. The site for visas here in Italy is: http://www.esteri.it/visti/index_eng.asp
. The site has links to the application, the additional information you need to supply in order to get the visa and where to apply. It also includes education visas which are somewhat easier to get than work visas. You can find similar information for other countries on their consulate websites. You can find other consulate websites with a fairly simple search. Note that you'll need to apply to the consulate that has jurisdiction over the state where you live, but you can find the necessary information on any of the consulate websites.
A work permit is separate - you cannot apply for that yourself. The company has to apply and they have to be able to demonstrate that there is not a viable EU candidate for the job. As a result, jobs for foreigners including Canadian or US citizens are pretty much restricted to people with special education, knowledge, or experience ... and you would have to be able to speak the local language. Right now, as noted above, the best bet would probably be something in the healthcare field. When I moved here, it was through a transfer of the job I was already doing in the US to the Italian office. Even so, it took 8 months to put all the paperwork in place to apply for a visa. If you already have a job offer, the company will provide you the information you need for your visa application and take care of things like work permits.
It's useful to check the expat sites for information about living and working in the places you might be interested in. You can find sites by searching for "expat" and the name of your target country. These sites will tell you how to register your address, provide information about healthcare, banks, and so forth to ease you into daily life.
One other thing to consider is that if you are a US expat, you will have to file tax returns both here and in the US which can be quite expensive. You'll want to look at the tax implications for the countries you select carefully.
As for a trip of a year or two, you would need a lot of funding since it would be illegal for you to work. You would also need to plan your route carefully. You can only legally stay in the entire Schengen zone for 90 days in any 180 day period so you would need to leave for the UK or another non Schengen country until you can legally return.