Nice looking cheese, my vote:
1) During the first few days of it's life it will give off a lot of moisture, but then, even at 85% RH it should feel dry on outside, especially if you've brine bathed which many do to add salt and start the formation of a natural rind. Hope your gauge is accurate at that high a RH.
2) As you've brine bathed you could go without waxing, if you have a well controlled cheese cave. If you don't then waxing gives you the extra protection against the elements, but your cheese needs to be reasonably dry before waxing otherwise you could get mold beneath the surface.
I don't think there is a big correlation between size and aging duration, I assume you want smaller to be able to eat some of the same cheese at 1, 3 and 6 months type thing, to see how's it's character matures. If you want to do that and only have one hoop size, I don't see any problem with cutting it disk wise fresh after pressing as long as min say 2 inch/5 cm height and waxing from there. Should you re-brine, depends if brining was just to add salt to the cheese in which case probably enough, or to form a rind in which case you probaby want to brine at least the new sides.