If I recall correctly, I purchased the shoes at the Bay for approximately $70. I think that really helps emphasize the factors you listed.
Are there any shoes that are decent in quality and can be shipped to Canada for a reasonable price? An "entry level" oxford perhaps?
Allen Edmonds Shoe Bank. They ship to Canada for $25 per pair. Only order 1 pair at a time or you will be charged taxes. Up your budget just a bit and you can get a pair for about $170.
Go to Harry Rosen and try on a few AE shoes to see how they fit and what size you are. Don't buy from them though as they sell for $400 with tax and all.