What you describe is called a collision. Collisions necessarily exist, since SHA-1 accepts many more distinct messages as input that it can produce distinct outputs (SHA-1 may eat any string of bits up to 2^64 bits, but outputs only 160 bits; thus, at least one output value must pop up several times). This observation is valid for any function with an output smaller than its input, regardless of whether the function is a "good" hash function or not.
Assuming that SHA-1 behaves like a "random oracle" (a conceptual object which basically returns random values, with the sole restriction that once it has returned output v on input m, it must always thereafter return v on input m), then the probability of collision, for any two distinct strings S1 and S2, should be 2^(-160). Still under the assumption of SHA-1 behaving like a random oracle, if you collect many input strings, then you shall begin to observe collisions after having collected about 2^80 such strings.
(That's 2^80 and not 2^160 because, with 2^80 strings you can make about 2^159 pairs of strings. This is often called the "birthday paradox" because it comes as a surprise to most people when applied to collisions on birthdays. See the Wikipedia page on the subject.)
Now we strongly suspect that SHA-1 does not really behave like a random oracle, because the birthday-paradox approach is the optimal collision searching algorithm for a random oracle. Yet there is a published attack which should find a collision in about 2^63 steps, hence 2^17 = 131072 times faster than the birthday-paradox algorithm. Such an attack should not be doable on a true random oracle. Mind you, this attack has not been actually completed, it remains theoretical (some people tried but apparently could not find enough CPU power). Yet, the theory looks sound and it really seems that SHA-1 is not a random oracle. Correspondingly, as for the probability of collision, well, all bets are off.
As for your third question: for a function with a n-bit output, then there necessarily are collisions if you can input more than 2^n distinct messages, i.e. if the maximum input message length is greater than n. With a bound m lower than n, the answer is not as easy. If the function behaves as a random oracle, then the probability of the existence of a collision lowers with m, and not linearly, rather with a steep cutoff around m=n/2. This is the same analysis than the birthday paradox. With SHA-1, this means that if m < 80 then chances are that there is no collision, while m > 80 makes the existence of at least one collision very probable (with m > 160 this becomes a certainty).
Note that there is a difference between "there exists a collision" and "you find a collision". Even when a collision must exist, you still have your 2^(-160) probability every time you try. What the previous paragraph means is that such a probability is rather meaningless if you cannot (conceptually) try 2^160 pairs of strings, e.g. because you restrict yourself to strings of less than 80 bits.