With the piston at the bottom of the cylinder, the less volume between the piston face, and the check valve, the better.
Think of it like this,
If your pump cylinder has a volume of 10 cu.in. , and you have 1 cu.in dead space in the "pump head", you have a compression ratio of 10:1 .
This means that in "theory" you could compress the air 10 times to 145psi max.
If you cut the dead space to .1cu.in. , then the compression ratio goes to 100:1 with an attendant increase in theoretical maximum pressure.
Now, bore size comes into play, as you have only so much mass to throw around.
See previous post.
To sum up,
Regardless of bore size and the weight you have to put onto the piston head, if you utilize a "largish" dead space design, you limit the compression ratio, and the ability of the pump to create pressure.
The floating o-ring design is better IMHO.

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