I don't know about shipping from Toronto to Lisbon. I know you can ship by sea. By air, there is no direct scheduled flight (there are charter flights though),
so there are several options (either through US or direct to a hub in Europe and forward from there).
I don't think you need a carnet for western Europe and this includes Portugal. You do need insurance when driving off once in Lisbon and I believe you can
arrange for Europe-wide insurance once there, or even do it in advance. This insurance is the green card insurance. I don't know if it'll cover countries
beyond Turkey (I doubt it).
As for border hassles, from Portugal all the way to Poland, there are none, as the border controls have been abolished years ago across most EU
(European Union) countries and two non-EU countries. These countries are called Schengen signatary countries. These are:
Portugal, Spain, France, The Benelux countries, Germany, Austria, Italy, Greece, Finland, Denmark, Norway, Sweden and Iceland.
The border checks have been eliminated between these countries, so if they share a land border, you'll either see only a sign saying where the border is,
or old empty border installations.
See more information at
The countries where there are border checks are:
UK, Ireland, Switzerland, Andorra, San Marino, Lichtenstein and all of eastern Europe.