Can you actually have both tet and dip pollen from a tetraploid conversion?
Yes. A tetraploid conversion can still be a mixture of diploid and tetraploid cells and produce both "diploid" and "tetraploid" pollen. A tetraploid conversion could produce little "tetraploid" pollen and mostly "diploid" pollen.
When buying a tetraploid conversion one might want to ask the seller what layers were converted (layer 1 or layer 2 or both and were they completely converted). One might also want to ask how long ago it was checked for ploidy.
Should I pay Jamie Gossard to test the ploidy?
I would wait until he is in a position to do actual chromosome counts of root tip squashes. He needs to confirm that the highly unusual results he is producing with the flow cytometry machine are related to differences in chromosome counts (to differences in ploidy) and not related to other factors.