jmc

Let the expected value of the number of times Bob rolls his die on a single day be $E$. When Bob rolls his die, there is a $\frac{5}{6}$ chance that he will stop rolling after one roll, and a $\frac{1}{6}$ chance that he will have to start over. In the second case, since his first roll had no effect on the outcome, Bob will on average roll his die $E$ more times, for a total of $1+E$ times that day. Therefore, we know that $E=\frac{5}{6}(1)+\frac{1}{6}(1+E)$, or that $E=\frac{6}{5}$. Over 365 days, Bob will roll his die an average of $\frac{6}{5}\cdot 365=\boxed{438}$ times total.