You might look into a specialized luggage place (yellow pages were a saver for me), they usually can hand out good advice. Or I suggest The Bay as well, but only buy when on 50-60% "sale" (i.e. every week-end

). And check out to buy some light luggage, with the weight restrictions getting lower and lower, you don't want a suitcase of 15 pounds! And don't feel like you need a complete set. I find 2*26 inch more practical than a 26+29 inch. The 29 inch is soooo big, and it's easy to get overweight.
Before my last trip, I got Air Canada Super Lite luggage in brown/beige at The Bay, made by Holiday Luggage. It's not top quality, but it's OK for 1-2 trips/year, and I got a good price: 20+26 inch for 120$+tax. My aunt also had a good experience with Holiday warranty when a suitcase broke, so it this comforting (not that it broke thought!

).
I also checked Hey's, the xCase line is pretty and light, but it would have run 200$ for 2 pieces (budget was TIGHT), and my boyfriend thought they looked like an old vacuum!!

He vetoed against them! There was also a light Skyway that I checked.
On your budget, if you need like 4-5 pieces, you could go over 100$ a piece, but then really look into a luggage store (not Bentley's), but a place where they sell and repair them. You'll get some advice on what should fit your needs AND your budget.
Good luck!