Say I pick a random $n\times n$ matrix with entries uniformly chosen from $[0, 1]$.
a) What is the probability it is nilpotent?
b) What is the probability that, given it is nilpotent, it is similar to a given matrix?
To clarify part (b), there are finitely many possibilities for it when written in Jordan normal form. What are the probabilities of each of these? (e.g. is there one of them that comes up with probability $1$?)
Edit: as Qiaochu pointed out, the probability it's nilpotent is $0$. So for part (b), can we say anything about the relative measure of the space of matrices with different Jordan blocks? For example, even if they both have measure 0, is it possible to say that the set of matrices similar to $\bigl( \begin{smallmatrix}0 & 1\\ 0 & 0\end{smallmatrix}\bigr)$ is larger in some concrete sense than those similar to $\bigl( \begin{smallmatrix}0 & 0\\ 0 & 0\end{smallmatrix}\bigr)$?
The nilpotent matrices form a variety of (I think) dimension $n^2-n$ in the $n \times n$ matrices (based on the fact that the coefficients of $\lambda^j$ for $j=0,\ldots,n-1$ in the characteristic polynomial must be $0$). You can then consider $n^2-n$-dimensional Hausdorff measure on this variety. Fix some nonzero vector $v$. If $A^k v \ne 0$ for $k = 1, \ldots, n-1$ then the Jordan form consists of a single block, and I'm pretty sure this will be the case for almost every nilpotent matrix.