GEOTOL - True Position of holes with 1 Planar Datum, reported results vary when dimensioning individually or grouped.

If it's a feature pattern (2x, 6x, etc), the callout refers not only to the orientation to datum A in your case, but also the location of the holes relative to each other.  In geo tol, if you select multiple features at once when calling out your GDT, it treats it as a feature pattern.

Ok, is there a way to not have it do that? Do I need to report each in GEOTOL individually? Even when I do this it reports an X,Y deviation, when in theory with only 1 defined planar datum to relate to - that makes no sense. I see nowhere on the print requiring relative dimensions of the hole pattern and I am reporting basic dimensions of the hole locations elsewhere. Would legacy dimensioning do the same?

Ok, is there a way to not have it do that? Do I need to report each in GEOTOL individually? Even when I do this it reports an X,Y deviation, when in theory with only 1 defined planar datum to relate to - that makes no sense. I see nowhere on the print requiring relative dimensions of the hole pattern and I am reporting basic dimensions of the hole locations elsewhere. Would legacy dimensioning do the same?

If the drawing shows the holes as a pattern then that is how you should be inspecting them.  Reporting the holes individually, which ever method you use (legacy or geometric tolerance command) would not be satisfying the design intent and could result in you accepting bad parts.

I see, thank you. The drawing calls out the hole position tolerance in a table with size, thread requirements, quantity, and positional tolerance - not with a FCF on the workpiece drawing itself, which seems a little ambiguous. 

I would say that, since the QTY is more than 1 for every option in that table, they should be inspected as patterns.  This would be the most conservative approach - meaning you might risk over inspecting but there would be no risk of you accepting bad parts.

also, it isn't a 'perpendicular' tolerance with just the "A" datum, but the position callout INCLUDES perpendicular as the position tolerance is not a circle but a cylinder, and both ends (and the middle) must pass, not just the top or bottom.

Thank you. I have a lot to learn!

don't we all?