What is the shortest program for which halting is unknown?
There is a 5-state, 2-symbol Turing machine for which it is not known whether it halts. See http://en.wikipedia.org/wiki/Busy_beaver.
You may find my blog post "Are small sentences of Peano arithmetic decidable?" relevant. In summary, John Langford and I investigated short sentences of Peano arithmetic. We enumerated them all (actually, our laptops did) and eliminated those that could be recognized as decidable. It quickly turned out that Diophantine equations were difficult to recognize as decidable. Among those we found two that gave a professional number theorist something to munch on (all quantifiers range over $\mathbb{N}$): $$\exists a, b, c . \; a^2 - 2 = (a + b) b c$$ and $$\exists a, b, c . \; a^2 + a - 1 = (a + b) b c.$$
The shortest unsolved sentence I am aware of is ($S$ is the successor function) $$\forall a \exists b \forall c, d . \; (a+b)(a+b) \neq S(S( (S(S c)) \cdot (S(S d)))).$$ It says (more or less) that there are infinitely many primes of the form $x^2 - 2$.
What I found most surprising was that mixed quantifiers were easier than just straight universal or existential statements. It seems that with very few symbols to spare for the matrix, you cannot produce an interesting mixed-quantifier sentence.
It's quite possible that the Collatz conjecture provides an answer. Apply this function repeatedly. The conjecture is that this process will eventually reach the number 1, regardless of which positive integer is chosen initially.
Not sure how many lines of code this would be. Probably 2 in Haskell.