My approach is I dose the basket and level. I then use the finger tip tripod method (finger tips on edge of piston and basket to feel the tamper compress). I'm sure the tamps are level, although I have a harder time getting a perfectly level tamp with the flat tamper

. I've been doing WDT to help rule out distribution.
The tampers are both cheapos. The flat is a solid stainless tamper and the convex is the budget lava tamp (bought on clearance and frankly a very comfortable tamper).
The pistons don't appear to be much different in size (mind you I lack calipers). If anything though the convex feels as it may be
slightly smaller, but again I lack any meaningful way to measure this.
While I've not done any scientific experimentation on this situation I have been as methodical with my technique as possible and still can't explain what I'm seeing.
I'll keep playing around with the tampers and see what happens. Thanks to you all for the feedback. I'm not overly worried about it, just its been a while since I've used the flat and I was surprised to see the things I was seeing.