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Cherry wood. Tried to find the best lighting I could, it's still not great. The taper on the shank is 0.5mm, is that still too much?

The transition and the bottom of your bowl are not right.
Here is a mental (or real, you can do this with a ball and cardboard) exercise.
The bowl of a billiard can be represented by the southern portion of a sphere from the South Pole to the Tropic of Capricorn with a truncated cone going north.
Form a cylinder of cardboard to represent the shank of the pipe. Fit this shank cylinder to the sphere portion so that it touches the South Pole. The area of contact will be a tear drop shape with the point at the South Pole and the round end up on the side of the sphere.
Your transition is square looking, with near vertical sides, and the bottom of the bowl has a boxy look.
DocAitch.

DocAitch is right. The bottom on your pipe should be spherical. It might be the picture, but it looks like your chamber was drilled at 90 degrees to the draft hole/smoke hole (or what ever its called). On the next one cant the bowl forward a couple of degrees.

Choosing to make a billiard is a good thing. There is tons of billiard making info available on this site. I suggest searching billiards in the gallery section, and reading comments on those as well.

That said, the cherry wood looks pretty. How does it smoke?

Ok, thanks for the mental exercise, I have been approaching the bowl all wrong. I did drill the chamber at a 3 degree cant to the draught hole, I just can't seem to take enough off the bowl to show it. I always end up stopping short.

The cherry smokes great. I haven't been a pipe smoker long but it reminds me of the cobs I got from MM. Smokes great from the first bowl, no break in or need for a coating. I started buying cherry wood turning blocks to use as practice since its cheaper, I can build a smokable pipe for about $3.50, including stem.