Yes, look into shipping from Canada...but you don't need to get to Halifax first, and it's not necessary to head for Europe enroute, or to spend weeks in a freighter cabin.
For whatever it's worth, shipping motorcycles is not a high priority for air freight companies anywhere (that I'm aware of) in the world. No matter what you do, it'll be expensive. And your 3 month trip is pretty marginal in terms of making it worthwhile to ship vs. rent--particularly round trip. You might also search this site for information on legal and/or semi-legal means for purchasing a bike on the spot in South America--there are at least a couple of reputable options in Colombia and Peru.
I'd add that riding through Central America to and from South America is not such a big deal, current Nicaragua situation aside, and shipping across the gap is expensive but not difficult. Your 3 month schedule doesn't really allow for that route, but if you had the time it'd be a worthwhile option. I've done it twice, and scores, maybe hundreds of riders do it every year.
Hope that's helpful.
Mark
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