Conceptually, it's a nice idea and many people have done it successfully. However, it isn't at all easy and depends a lot on where you're from and where you want to go. With the current world economy, it is particularly difficult.
For example, EU citizens have the right to live and work within the EU, but others need a visa to live and work here legally. I moved to Italy so the specifics here apply to that, but it's similar elsewhere in Europe. You can't just decide to relocate to Italy and go. The site for visas here in Italy is: http://www.esteri.it/visti/index_eng.asp . The rules in much of the EU have been harmonized and will be similar. You can also check the website of the consulate that has jurisdiction over you for other information. You cannot apply for the visa from Italy; you need to do that before you arrive. When you get here, you will have to apply for a Permesso di Soggiorno (Permission to Stay) from the authorities.
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. The medical/healthcare field may have the most demand right now. Positions in a field that you don't have any special qualification for would be unlikely - especially without knowing the language. When I applied for a visa several years ago, the process took about 8 months even though it was just of transfer of the job I was already doing from the US to Italy. Your best bet might be to work with an international company that has offices both there and here where you might be able to transfer. However, you wouldn't be able to do this as a temporary employee and you're not going to get room and board.
It's useful to check the expat sites for information about living and working here or other places you might be interested in:
http://www.escapeartist.com/
http://www.expatica.com/
http://www.expatsinitaly.com/
There are similar sites specific to just about any country you might be interested in that you can find by searching for "ex pat" or "expat" and the name of the country. Generally, these will have a lot of good information on daily life and negotiating the bureaucracy when you arrive and provide you with useful information you should know before you make the transition.
If you're starting from Europe and want to go to the US, there is also a complicated immigration process going in that direction.

