In my experience, an 8 bay (DB8) will be easier to aim than an Yagi (91XG). The 8-bay will also pick up a wider grouping of channels.

Depending on how close the hill is, the VHF stations may bend over it. From what I have seen, VHF is more forgiving to terrain obstruction than UHF.

Something else for me to consider is I have a bunch of towers with a strong signal to the east that are close together. So Im wondering if the 8 bay would be a better choice vs the 91XG. As you said it might be harder to point.