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This is covered in the "Redundant Conditions" Sidebar on Page 623.
REDUNDANT CONDITIONS
You can have a given condition only once at a time. If
an effect would impose a condition you already have,
you now have that condition for the longer of the two
durations. The shorter-duration condition effectively
ends, though other conditions caused by the original,
shorter-duration effect might continue.
For example, let’s say you have been hit by a monster
that drains your vitality; your wound causes you to be
enfeebled 2 and flat-footed until the end of the monster’s
next turn. Before the end of that creature’s next turn, a
trap poisons you, making you enfeebled 2 for 1 minute. In
this case, the enfeebled 2 that lasts for 1 minute replaces
the enfeebled 2 from the monster, so you would be
enfeebled 2 for the longer duration. You would remain
flat-footed, since nothing replaced that condition, and it
still lasts only until the end of the monster’s next turn.
Any ability that removes a condition removes it
entirely, no matter what its condition value is or how
many times you’ve been affected by it. In the example
above, a spell that removes the enfeebled condition from
you would remove it entirely—the spell wouldn’t need to
remove it twice.
Redundant Conditions with Values
Conditions with different values are considered different
conditions. If you’re affected by a condition with a
value multiple times, you apply only the highest value,
although you might have to track both durations if one
has a lower value but lasts longer. For example, if you
had a slowed 2 condition that lasts 1 round and a slowed
1 condition that lasts for 6 rounds, you’d be slowed 2 for
the first round, and then you’d change to slowed 1 for
the remaining 5 rounds of the second effect’s duration. If
something reduces the condition value, it reduces it for
all conditions of that name affecting you. For instance, in
this example above, if something reduced your slowed
value by 1, it would reduce the first condition from the
example to slowed 1 and reduce the second to slowed 0,
removing it.
I've bolded the relevant text.
In short you cannot suffer from the same condition multiple times. In the case of 2 similarly "timed" abilities, you suffer the longer duration. If you have 2 different conditions with different values, you suffer the worst of the two. If those conditions have different durations you may have to track both durations, especially if the higher value condition has a lower duration.
If you are cured of the condition, you are cured from all instances of that condition.
Edit: So far as your question regarding multiple demoralizes, you would apply these rules. If one character rolled a critical success whereas the other rolled a success, apply the critical success. If the character that rolled a success has any secondary effects that trigger from Demoralize, you would also apply those even if their instance of fear was ignored in the "stack" of conditions.
@Superbidi: Don't worry too much. I activated my Ninja Powers. :)
No, they don't stack. Only the highest prevail.
Conditions don't "add" themselves. So, if you are already Frightened, you can be Frightened again with no effect (unless you are Frightened with a higher value).
Also, be careful as some conditions give the same maluses. Frightened doesn't stack with Sickened, and overrides Clumsy and Stupefied with lower values, for example.
So, in general, in PF2, it's better to only give one such conditions to an enemy.
Edit: I've been too Clumsy :)
Yeah, many conditions give the same kind of penalty which wont stack and the same penalties do not stack to give larger values.