It's custom pipes - yeah, angle the draft hole up just a hair if you can, then drill the chamber down to meet it, this is the best sure-fire way to make the connection and have lots of wood where you need it.
In terms of ideals, roughly, the mathematics of a billiard are that the bowl height measured from the shank should be the same length as the shank measured from the bowl, and probably you want the bowl in total to be something like 4 times (maybe not quite) as tall as the shank. Stem length (again ideal, you can find all kinds of variations that work) is same as stummel length.
When you start to hit these things, the pipes sell pretty fast is my experience.
Then once you have that basic formula, once it's really in your blood, you can start understanding other shapes, dublins, Canadians, whatever, as variations of that, and squash them, pull them, stretch them, whatever it is, and come out with pipes that still look "right"
If you break this Canadian down, you will see that even though the shank is long (stretched) and oval (compressed), the basic proportions come back to the billiard formula (imagine the pipe had a billiard shank, etc, and you'll see that the total length, for example, is "correct").
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