Hi , from a new member. I think it's best to not enlarge this hole for a larger bolt. Basicly 2 reasons: 1 There is not enough of a shoulder around the hole for a larger bolt. 2 the shaft head piece and the tiller mount bracket has an interference fit which is what should control free play, the bolt is merely the hinge and attachment point. If you should enlarge the bolt to control slop it will right up to the point where the tiller mount will break out by the holes youv'e enlarged. You will have all the tiller leverge on the bolt holes running through the tiller mount and not shared evenly over the shaft head.
In your first picture the wear is evident in this area and needs some shiming. Maybe this helps. Carl