So, based on the bevy of responses , my guess is that the way that I did it is the best way for now.
What I had to do to show this functionality was:
1) Create the Hole Callout, add some blank lines between the two line items.
2) Create and attach the bottom Geometric Callout (.001)
3) Create the .020 Geometric Callout and place it in space
4) Drag the Hole callout over the .020 Geometric Tolerance until it is in place.
5) Select both items (The Hole Callout and the .020 Geometric Tolerance), Right Mouse Button, and select "Group". (This groups them together and allows the .020 tolerance to move around with the hole callout)
I will be putting in an enhancement request for this functionality in the future.
This might also work to keep everything linked and displayed as one element (I'm working from memory, so I didn't get a chance to test this out):
1) Create one hole callout. Delete the second line.
2) Create a second hole callout. Delete and remove the first line.
3) Create a Note annotation.
4) While editing the note, on the first line, select the first hole callout.
5) On the second line of the note, create a GTOL within the note using the GTOL button in PropertyManager. It creates a Feature Control Frame in the same way as Geometry Tolerance command, but the FCF is embedded in the note.
6) On the third line on the note, select the second hole callout.
7) On the fourth line of the note, create your second GTOL FCF in the same way as above.
8) Accept your note.
9) Select each of your original hole callouts and hide them.