So you'll be leaving Toronto on the 14th and returning to Edmonton on the 18th? You can easily book multi-city flights online (i.e. Westjet) -- no need to use a travel agent (unless you want to of course).
5 days (4 nights) including travel isn't a ton of time, so you probably don't want to waste two of those days in transit. The Carribbean would be too far, and Orlando would be pushing it IMO. I would also strike SF and Vegas from your list -- it's probably a lot more convenient (and cheaper) to take those trips from Edmonton versus Toronto.
If you're going to be in the East, you should take advantage of being in that area. Any interest in going to New York (Manhattan)? It'll be more expensive than other cities, but the experience is worth it IMO.
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