Further to the "for each" discussion above, the purpose of that ruling is to illustrate that Wingfoot can wound the same minion more than once, if you choose. So the same logic can be applied to FNF, since that old ruling is no longer in the CRD.
Just because the ruling doesn't appear in the most recent CRD, I don't think that means we can ignore it. It's the only official ruling we have on the matter, and it was never reversed. Plus, other official rules which are still in effect (such as the Movie Block X-list) appear in older CRDs but not the most recent one. So, just because it isn't in the latest CRD, doesn't mean it's no longer in effect.
And if you're drawing a
Wingfoot comparison with "for each" actions,
Clever Hobbits is also a "for each" action, which would seem to indicate the card can attempt to discard the same condition more than once.
Also, since Clever Hobbits has discarding the conditions as a cost of its action, it doesn't fall under the "do as much as you can and ignore the rest" clause.
I was about to say you have a brilliant point there... but then I saw this under "costs" in CR:
If a player is paying costs for a card and a
response action occurs which modifies those
costs, that player must continue to pay as many
costs as he can, even if it is no longer possible to
pay them all.
Easy way to solve this, replicate the situation on Gemp, then see what it lets you do 
Ha! I am quite certain Haszor is being facetious. Gemp does whatever MarcinS tells it to.
ETA: I'm looking though the CR and the various CRDs to see if any other related rulings may shed some light on this. Here's one that is interesting to me (from CR):
PLUNDERED ARMORIES 1 C 193
If a minion bearing a ? weapon is discarded
due to losing a skirmish,
Plundered Armories takes effect before optional actions triggered by
winning/losing that skirmish occur.
When an effect discards "all" minions (thereby
discarding their weapons), they are discarded
at the same time. None of those minions may
have weapons played on them with Plundered
Armories.It seems like a comparison could be drawn to cards that discard "all" conditions, or "all" shadow conditions (such as
Deep in Thought,
Saruman's Power, etc.).
Here is the aforementioned ruling on
FNF:
FORTRESS NEVER FALLEN 4 U 276
The effect of this condition's special ability
when the card has more than one token is
simultaneous. Several conditions are discarded
at the same time. Siege Engine responds to these
discards by preventing all of them.You have three tokens on
Fortress Never Fallen when you use its special ability. You select three
Shadow conditions to be discarded (including my
Siege Engine), and discard
Fortress Never Fallen.
I use the response special ability on
Siege Engine,
which technically saves all three conditions, but
then I discard
Siege Engine to pay its own cost.