Hi All,
hmmm, where to start?
firstly, good luck with your trip. It is really hard to rock up and "meet locals". Most of the people you'll meet wll be other travelers. If you want to meet locals, couch surfing is the only way to go as hostels are full of other travelers from every country but the one you are visiting.
Now to your questions, I don't think you should worry. Just take it as it comes and you will have a good time. Being Canadian, it is pretty easy. You don't even need a visa and can just rock up to Europe. Once in Europe, there are no borders or checks between Spain and Italy so it should be seamless.
Most of your journey will be by train. Google is your friend here. Look up train timetables between all your destinations and decide if that is acceptable to you. For example, Barcelona to Paris would be a long trip. You might want to consider booking a flight for this leg of the trip. I don't tend to over plan it. Bring a ipod / ipad / iphone or laptop and research transportation the day before you are due to depart.
If I were you, I would book the first hostel for maybe three nights. September is shoulder season and hostels should be readily available (except for some weekends). The day you are due to depart a city, you can go online to hostelworld or hostelbookers or couchsurfing and book the next place.
If you are unsure how to get to your destination once arriving at an airport, go to the airport information desk and they will help you get to where you want to go. All airports have transport links (other than taxis) which go to downtown. It is incredibly nerve racking taking public transport to your destination when you first arrive but you'll get used to it.
Don't plan it by country, plan it by city. Min. 4 days are required for the larger cities.
Get a couple Rick Steves books. You'll get more useful info from them than anywhere. And I agree with Morro: if you want to meet the locals, go couchsurfing.
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