I can't say that I was particularly systematic, but my general approach was to try to construct two rank deficient matrices $A$ and $B$ such that $\left\| {AB} \right\|_2$ would be small relative to $\left\| A \right\|_2 \left\| B \right\|_2$. The thought was that this would increase the likelihood that $\left\| {\left( {AB} \right)^{\dagger} } \right\|_2$ would exceed $\left\| {B^{\dagger}} \right\|_2 \left\| {A^{\dagger}} \right\|_2$.