I asked a friend of mine who is married to a woman from Japan, and frequents the country regularly. I asked him for his views:
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Rules I have seen laid out:
1. Make it a consumable.
1.1 Make each item very similar. See NOTE below.
2. Make it something expensive with a label on it.
3. Don't make it homemade (unless you know the receiver).
With that said, here are my experiences.
As cliched as it is, nothing can go wrong with the gift of maple. Laura Secord has some good, albeit typical, omiyage (souveniers). Maple leaf shaped anything works. Chocolates, hard candy, sugar. It all works well. Sobeys and other stores have maple flakes in the syrup section.
Light and non-breakable.
Dollarama used to sell Maple Cream Cookies, 350 grams for a buck. Labelled "from Canada" and everything. Now the label is not so good, something about "processed in Canada", and there's a big ol' Dollarama $1.50 tag printed right on the packaging. Depending on the closeness of the recepients, these still might work. They are still just as good as the Dare ones that can be bought at Superstore for $3.50. Relatives still love them.
Japan is a country of two chocolate bars: Snickers and KitKat. Tell this guy, as a side note, that about 50 different kinds of Kit Kats are available in the land of the rising sun. Don't leave Narita before hitting the shopping area in the arrivals area. So, any different chocolate bar might work, depending on the audience. Cadbury's Fruit and Nut Bar go along way with the in-laws.
Rice Krispie Squares. Seriously, a box of Rice Krispies, a couple bags of marshmallows (they are outrageously and I mean outrageously expensive in Japan, if they can be found at all), margarine (no need to pack, this can be found in Japan), someone's kitchen and the time to make them, friends for life made. In a pinch, a box of pre-made ones work well. It is rice, after all.
Smoked salmon. It's ridiculously expensive at YVR, super cheap at Superstore before travel.
Salmon jerky. Should be easy to find in Calgary.
Ice wine. Difficult to transport, wins hearts, though.
This also is cliched, but the art of omiyage is that "it's the thought that counts". The very fact that you thought about bringing something weighs far more heavy than the item itself. Keep it sweet, keep it small, make it thoughtful. Maybe wrap it up neatly, but this is a first time visit, ignorance of the rules can be broken as the Japanese won't be expecting the gifts.
NOTE:
A thing to potentially get caught on: if the recipients know each other, they will compare. Watch this as this can be seen as favoritism.
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