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Help with planning for a future move (Lisbon)

Hey guys,

Sometime within the next couple of years I'd like to live in Lisbon for at least half a year in order to help myself become fluent in Portuguese and also have the experience of living there before I settle down with my girlfriend and start a family.

My biggest issue is I have no idea where to even begin planning and was hoping someone who went through a similar situation could help me out a bit, which is why I joined this forum. :)

I'm studying accounting in Canada at the moment and should be graduating soon, preferably I'd like to live on my own in Lisbon and if possible work with something in the field of business but this isn't necessary. By the time I'd move to Lisbon, I expect to be well educated in speaking Portuguese as I will be using Rosetta Stone & the help of my parents.

I was just wondering if expecting all that is realistic? To find a job I can work at for at least 6 months, live on my own in Lisbon, and if possible work in business?

Are finding jobs really hard in Lisbon? Would living on my own be too expensive?

Any help is greatly appreciated! :)