Looking deeper, and beginning to over think.........

armyjeep101 in images (small) uploaded in admin
armyjeep102 BAD in images (small (unless that's the one uploaded in admin))
armyjeep101_MED is good
armyjeep101_LRG is good

Either is good, but ONLY if the small in images is armyjeep101 OR armyjeep102 - I can't have more than 1 armyjeepxxx in images (small). If I have armyjeep102, 103 etc, they get ignored and the only armyjeep10x_MED and _LRG (whichever one was administratively uploaded) are going to be the extras

Wow, articulation is getting difficult......

ok, let's try this:

armyjeep101 uploaded in admin

therefore

armyjeep101_MED
armyjeep101_LRG
armyjeep102_MED
armyjeep102_LRG
armyjeep104_MED
armyjeep104_LRG
and on down the line are all good UNTIL.....
armyjeep111_MED /_LRG is bad because we left the armyjeep10x and entered into the armyjeep11x twilight zone?

Which means, I need to rename to something like

armyjeep1_01 small in images
armyjeep1_01_MED
armyjeep1_01_LRG
and on down the line are all good EVEN when.....
armyjeep1_11_MED
armyjeep1_11_LRG

then, the mighty Zen pats me on the back and rewards me with a big chocolate cookie?