Aamco wasn't able to reproduce the issue. But by my description, they are "firmly" convinced it is hydraulic and NOT the transmission(syncros)
They found no leaks and the trans was full.
I did a visual check on the rubber line in the circuit and it appeared to be in good condition(ie no hose expansion causing the issue)
I will not discount that I may not be fully pushing the pedal to the carpet. I will try bleeding it.