In reality there is little risk of an originally good wheel becoming dangerously undercut.
These devices need a flat or near flat grinding surface to function.
Any significant hollowing will destroy the sharpening geometry leading to loss of clearance angle at the outer edges so "sharpening" the drill will make little difference to its cutting prowess. The larger the drill the sooner the effect occurs. Long before the wheel becomes dangerous the "(obscenity delated) useless sharpener thing" will have been binned, pitched into orbit or relegated to the darkest, most spider infested, corner at the back of the cupboard.
A barely noticeable hollowing of the side of the flat wheel I originally had on my grinder was sufficient to prevent proper sharpening of larger drills. Careful examination under magnification proved that there was no clearance at the outer ends of the cutting edges. I'd guess something significantly under 1/16" hollow would be enough to destroy all confidence.
I fitted a 3/8" (ish) wide straight cup wheel and wide table perpendicular to the spindle, Hemingway Worden style., to my inexpensive Whitecolt grinder. Which made it far nicer to use for tool sharpening duties. The better visibility made it clear that the actual cutting circle travels sideways across the wheel as the Picador device swings. With 20/20 hindsight my cup wheel was barely wide enough to manage 1/2" drills. Had to do a bit of careful shuffling of pivot mount position to get it all working well.
I suspect the Picador vertical pivot, 5 to 5 edge position, style has a rather greater shift of the cutting point during the swing than the alternative angled pivot, vertical edge position, style. Making it considerably more sensitive to wheel hollowing. But the Picador grind geometry is much more reliable over a range of drill sizes.
Clive