What the Rules Say
Whenever you take damage while you are concentrating on a spell, you must make a Constitution saving throw to maintain your concentration. The DC equals 10 or half the damage you take, whichever number is higher.
Means that when you have taken damage. This is different than other effects that happen "when you are hit" like Shield:
Casting Time: 1 reaction, which you take when you are
hit by an attack or targeted by the magic missile spell
This difference, as evidenced by the two difference sets of language, mean that the order is:
- You are hit
- Reactions and effects that trigger on hit
- Take damage (HP changes)
- Reactions and effects that trigger on damage
this is covered in a question about Hellish Rebuke: Hellish Rebuke reaction with zero hitpoints
In This Case
The above applied means that the druid who takes damage that drops their wild shape form would use their own, not the beast form's, CON Save for the check. Both would be Bob's Con.
So following the list...
30 damage
- Hit happens.
- No on hit events.
- Damage happens, reduced to zero, form dropped.
- Concentration check against Bob's CON Save vs DC 15.
60 Damage
- Hit happens.
- No on hit events.
- Damage happens, reduced to zero, form dropped, Bob takes 30 rollover damage.
- Concentration check against Bob's CON Save vs DC 30.
Extra example to prove case
There is an class feature in Barbarian class:
Retaliation. Starting at 14th level, when you take damage from
a creature that is within 5 feet of you. You can use your reaction to make a melee weapon attack against that creature.
Given this, following the idea Miniman posted that taking damage effects happens before the damage. The Barbarian is reduced to zero, and then gets a reaction (after being knocked unconscious) that allows him to make another attack. When it is clear that the barbarian would be eating dirt not still swinging.