For the first question, the strong topology is the polar topology generated by all weakly bounded subsets. The weakly bounded subsets of $E$ are also weakly bounded in $E^{\ast\ast}$ since $E\subset E^{\ast\ast}$ and they have the same dual space $E^{\ast}.$ Therefore $\beta(E^{\ast},E^{\ast\ast})$ is finer than $\beta(E^{\ast},E).$
For the second question, did you try the space of test functions, i.e, infinitely differentiable functions with compact support? More generally, Hausdorff barrelled spaces have the property you want, so you should look for spaces in the class of barrelled spaces.
