I love my step through Ridgeback (it's a hybrid but I fitted a touring style seat, upright position, 21 gears), but I don't know how widely available they are in Canada.

You saying that you're happy at medium distances but hate the first 5k has really cheered me up, because I have just realised the same is basically true of me. (It's unfortunate that wherever I try to cycle hereabouts, there is basically a big hill in the first 5k, but that's the Pennines for you...)