Scrolling of the terminal does not always stick to the bottom
Solution 1:
The issue here is that the scroll is still going when the text continues to be output. The trackpad is still in a "scroll mode" in which Terminal doesn't check the position and waits until it's done.
This was originally so it would wait until your fingers are off the trackpad/you stop scrolling. With inertia scrolling, this scroll mode doesn't end until the velocity reaches 0. So, the terminal waits until it is 0, by which time the output has increased and it won't stick to the bottom. (This isn't as noticeable in Terminal due to the lack of rubber banding.)
So I guess it would technically be expected behavior but it is still undesired behavior :P
Solution 2:
Not related to the trackpad, but you can use your keyboard to scroll to the bottom of the document and be sure it sticks to it!
Press fn + RightArrow