It tends to be a little more complicated than that. For starters, I assume you will have Mrs. Toolguy bringing back some? The personal exemption for cigars into Canada is 50 per ADULT (A rule I feel they invented because of me). If you are over the exemption amount, you don't get to decide which ones fall under the exemption, but rather they take the total value of all the cigars and make up some random number (I am sure there is some convoluted math here)
Some other things to think about. If you are hunting for larger or more expensive cigars keep in mind that if you go over your personal exemption for total amount of dollars into Canada, you will be f$#@!d. Your cigar exemption is not in addition to your personal amounts for dollars of imported goods.
Besides that, if you search around the forum a bit, you will notice that larger vitolas can be difficult to find as these get chewed up by the US market. If you want to find some truly aged gems, hunt for some of the classic vitolas. You may be surprised what you find.
As always, I usually just declare everything I bring, even when I am over my limits, and have never been charged for any of it. This is usually an extra box per person. I wouldn't try to bring a whole pile back. You can almost always meet a mule or two at the resort that will be on the same return flight as you. I have used this strategy many times and find it easier than anything else.
My 2 cents! Hope it helps.