Threes case:

Caroline    David       Jordan
Don't Know, Don't Know, Don't Lose
Don't Win

Caroline saying Don't Know means that either David or Jordan
(or both) has a card larger than a 2.  Similarly, David saying
Don't Know means that either Caroline or Jordan has a card
larger than a 2.  In addition, David saying Don't Know also
means that if Jordan has a two, that Caroline must have a
card larger than a three, else David would have said
Don't Lose.  If Jordan saw a pair of twos, he would
have said Win since he knows he has a card greater than a
two.  If he saw a two and a card greater than a three, he 
would have to say Don't Know because his card could be a
three, or King (for example).  Thus he must see either a pair
of threes, or a three and a two.  If he sees either person has
a two, he knows he beat that, and at least tied the three, so
he can say Don't Lose.  If he sees a pair of threes, he
knows he must have a three or better, since if he only had a
two then David would have said Don't Lose.  So at the end of
the first round, the remaining possibilities to a blind
observer are:

   2 3 3+
   3 2 3+
   3 3 3+

Next, Caroline says Don't Win.  She knows she has a two
or a three at this point, so clearly Jordan doesn't have
a card larger than a three, so he must have a three.
Also, David does not have a two, because otherwise she
would have said Don't Lose.  So David must have a three.

At this point we do not know if Caroline has a two or a
three.  David and Jordan know, of course, but their
subsequent answers, Tie for both, do not let us
know as a blind observer.  The game can continue from
this point forever, with Caroline always saying
Don't Win and the other two always saying Tie, and
neither Caroline nor the blind observer will never
know what card Caroline has.

Fifth problem:

Eight Don't Knows in a row require some amount of systematic
approach to our analysis.  To eliminate the top set is
straightforward.  Caroline saying Don't Know the first time
means neither David nor Jordan have an Ace.  David saying
Don't Know next means neither Caroline or Jordan have a
King or higher.  Jordan saying Don't Know next means neither
Caroline nor David has a Queen or higher.  This continues,
until after the eighth Don't Know, we know that Caroline
and Jordan both have a 6 or lower, and David has a 7 or
lower.

The lower cards are slightly more complicated.  Caroline
saying Don't Know first means that *,2,2 is eliminated.
David saying Don't Know means that 2,*,2 and 3,*,2
are eliminated.  3,*,2 is eliminated because otherwise
David would know he at least tied.  Jordan saying Don't
Know eliminates all cases where Caroline and David both
have 3 or less.  That's the first round.

In the second round, Caroline saying Don't Know again
eliminates all the cases where David has 3 or less and
Jordan has 4 or less, as well as the cases where
David has 4 and Jordan has 2.  David saying Don't Know
then eliminates all the cases where both Caroline and
Jordan have 4 or less, *and* the cases where Jordan
has 2 and Caroline has 5 or less.  Jordan saying
Don't Know then eliminates the cases where both Caroline
and David have four or less, and also the cases where
Caroline has 5 and David has 3 or less.

In the third round, the analysis becomes more complicated,
but after the next two Don't Knows, the only remaining
cases are Caroline holding 5 or 6, David holding
4, 5, 6, or 7, and Jordan holding 6; all eight cases are
possible at this point.  Jordan saying Win indicates
that the other two must hold cards less than 6, so
Caroline must hold a 5, and David might hold a 4 or a 5.

Analysis of all cases:

[Don't Lose,Win/Tie,Win/Tie,Win/Tie] (1)
 2 2 2
[Don't Lose,Lose,Lose,Win] (12)
 3-A 2 2
[Don't Win,Win,Lose,Lose] (144)
 2-K A 2-K
[Don't Win,Win/Tie,Lose,Win/Tie] (12)
 A A 2-K
[Don't Win,Don't Win,Win,Lose,Lose] (144)
 2-K 2-K A
[Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (12)
 A 2-K A
[Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (13)
 2-A A A
[Don't Know,Win,Lose,Lose] (11)
 2 3-K 2
[Don't Know,Lose,Lose,Win] (143)
 A 2 3-K
 A 3-K 2-K
[Don't Know,Don't Lose,Lose,Win/Tie,Win/Tie] (1)
 3 3 2
[Don't Know,Don't Lose,Lose,Lose,Win] (10)
 3 4-K 2
[Don't Know,Don't Win,Win,Lose,Lose] (121)
 2-Q 2-Q K
[Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (11)
 2-Q K K
[Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (120)
 K 2 3-Q
 K 3-Q 2-Q
[Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (11)
 K K 2-Q
[Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (12)
 K 2-K K
[Don't Know,Don't Know,Win,Lose,Lose] (10)
 2 2 3-Q
[Don't Know,Don't Know,Lose,Lose,Win] (119)
 2-3 K 3-Q
 4-Q K 2-Q
[Don't Know,Don't Know,Don't Lose,Win/Tie,Lose,Win/Tie] (1)
 3 2 3
[Don't Know,Don't Know,Don't Lose,Lose,Lose,Win] (27)
 2 3 4-Q
 3 2-3 4-Q
[Don't Know,Don't Know,Don't Lose,Don't Win,Win/Tie,Win/Tie] (2)
 2-3 3 3
[Don't Know,Don't Know,Don't Win,Win,Lose,Lose] (99)
 Q 2 3-J
 Q 3-J 2-J
[Don't Know,Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (10)
 Q 2-J Q
[Don't Know,Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (98)
 2-3 Q 3-J
 4-J Q 2-J
[Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (10)
 2-J Q Q
[Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (11)
 Q Q 2-Q
[Don't Know,Don't Know,Don't Know,Win,Lose,Lose] (24)
 4-J 2 3
 4-J 3 2-3
[Don't Know,Don't Know,Don't Know,Lose,Lose,Win] (96)
 2-3 4-J Q
 4-J 2-J Q
[Don't Know,Don't Know,Don't Know,Don't Lose,Win/Tie,Lose,Win/Tie] (1)
 4 4 2
[Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Win/Tie,Win/Tie] (2)
 4 2-3 4
[Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Lose,Win] (21)
 5-J 2-3 4
 5-J 4 2
[Don't Know,Don't Know,Don't Know,Don't Win,Win,Lose,Lose] (79)
 2-3 J 3-10
 4-10 J 2-10
[Don't Know,Don't Know,Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (9)
 J J 2-10
[Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (77)
 2-3 4-10 J
 4-10 2-10 J
[Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (9)
 J 2-10 J
[Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (10)
 2-J J J
[Don't Know,Don't Know,Don't Know,Don't Know,Win,Lose,Lose] (20)
 2-3 4-10 3
 4 5-10 2
[Don't Know,Don't Know,Don't Know,Don't Know,Lose,Lose,Win] (74)
 J 2-3 5-10
 J 4 3-10
 J 5-10 2-10
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Win/Tie,Lose,Win/Tie] (2)
 2-3 4 4
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Win/Tie,Win/Tie] (1)
 5 5 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Lose,Win] (29)
 2-3 5-10 4
 4 5-10 3-4
 5 6-10 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Don't Win,Win/Tie,Win/Tie] (2)
 4 4 3-4
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win,Lose,Lose] (60)
 2-3 4-9 10
 4-9 2-9 10
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (8)
 2-9 10 10
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (57)
 10 2-3 5-9
 10 4 3-9
 10 5-9 2-9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (8)
 10 10 2-9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (9)
 10 2-10 10
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win,Lose,Lose] (25)
 2-3 4 5-9
 4 2-4 5-9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Lose,Lose,Win] (54)
 2-4 10 5-9
 5 10 3-9
 6-9 10 2-9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Win/Tie,Lose,Win/Tie] (2)
 5 2-3 5
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Win/Tie,Win/Tie] (3)
 2-4 5 5
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Lose,Win] (20)
 2-4 5 6-9
 5 2-3 6-9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win,Lose,Lose] (42)
 9 2-3 5-8
 9 4 3-8
 9 5-8 2-8
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (7)
 9 2-8 9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (39)
 2-4 9 5-8
 5 9 3-8
 6-8 9 2-8
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (7)
 2-8 9 9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (8)
 9 9 2-9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win,Lose,Lose] (17)
 5-8 4 3-4
 6-8 2-3 5
 6-8 5 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Lose,Lose,Win] (35)
 2-4 6-8 9
 5 4-8 9
 6-8 2-8 9
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Win/Tie,Lose,Win/Tie] (3)
 5 5 3-4
 6 6 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Win/Tie,Win/Tie] (2)
 6 2-3 6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Lose,Win] (18)
 6-8 4 5
 6-8 5 3-5
 7-8 2-3 6
 7-8 6 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Don't Win,Win/Tie,Win/Tie] (2)
 5 4-5 5
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win,Lose,Lose] (26)
 2-4 8 5-7
 5 8 3-7
 6-7 8 2-7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (6)
 8 8 2-7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (22)
 2-4 6-7 8
 5 4-7 8
 6-7 2-7 8
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (6)
 8 2-7 8
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (7)
 2-8 8 8
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win,Lose,Lose] (13)
 2-4 6-7 5
 5 6-7 3-5
 6 7 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win/Tie,Lose,Win/Tie] (1)
 7 7 2
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Lose,Lose,Win] (17)
 8 2-3 7
 8 4-5 6-7
 8 6 3-7
 8 7 2-7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Win/Tie,Lose,Win/Tie] (3)
 2-4 6 6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Win/Tie,Win/Tie] (3)
 6 6 3-5
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Lose,Lose,Lose,Win] (6)
 2-4 7 6
 6 7 3-5
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win,Lose,Lose] (11)
 2-4 6 7
 5 4-6 7
 6 2-6 7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win/Tie,Win/Tie,Lose] (2)
 7 2-3 7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Win/Tie,Lose,Win/Tie] (5)
 2-6 7 7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win,Lose,Lose] (6)
 7 4-5 6
 7 6 3-6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Win/Tie,Lose] (4)
 7 7 3-6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Win,Don't Win,Win/Tie,Don't Win,Win/Tie] (4)
 7 4-7 7
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win,Lose,Lose] (2)
 5 4-5 6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win/Tie,Win/Tie,Lose] (2)
 6 4-5 6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Win/Tie,Don't Win,Win/Tie] (2)
 5-6 6 6
[Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Don't Know,Lose,Lose,Win] (2)
 5-6 7 6