In short, my question is:

What is the shortest computer program for which it is not known whether or not the program halts?

Of course, this depends on the description language; I also have the following vague question:

To what extent does this depend on the description language?

Here's my motivation, which I am sure is known but I think is a particularly striking possibility for an application to mathematics:

Let $P(n)$ be a statement about the natural numbers such that there exists a Turing machine $T$ which can decide whether $P(n)$ is true or false. (That is, this Turing machine halts on every natural number $n$, printing "True" if $P(n)$ is true and "False" otherwise.) Then the smallest $n$ such that $P(n)$ is false has low Kolmogorov complexity, as it will be printed by a program that tests $P(1)$, then $P(2)$, and so on until it reaches $n$ with $P(n)$ false, and prints this $n$. Thus the Kolmogorov complexity of the smallest counterexample to $P$ is bounded above by $|T|+c$ for some (effective) constant $c$.

Let $L$ be the length of the shortest computer program for which the halting problem is not known. Then if $|T|+c < L$, we may prove the statement $\forall n, P(n)$ simply by executing all halting programs of length less than or equal to $|T|+c$, and running $T$ on their output. If $T$ outputs "True" for these finitely many numbers, then $P$ is true.

Of course, the Halting problem places limits on the power of this method.

Essentially, this question boils down to: What is the most succinctly stateable open conjecture?

EDIT: By the way, an amazing implication of the argument I give is that to prove any theorem about the natural numbers, it suffices to prove it for finitely many values (those with low Kolmogorov complexity). However, because of the Halting problem it is impossible to know which values! If anyone knows a reference for this sort of thing I would also appreciate that.