I really do not think there is much of a wake problem at the intersection on the down side of the hourglass. If this was a problem, this would be encountered on a fairly regular basis by most fliers. Yes, in calm or near calm conditions, there will be some turbulence left over on the climbing leg, but on every hourglass flown (at least ones that have a real intersection), the down leg will encounter air that was "disturbed" on the up leg of that hourglass.
There are various kinds of turbulence that can upset our models. I think that we are all familiar with the occasional thermal that will cross our circles when a model is in the air. These can be fairly mild affairs that are barely noticeable to those that blow lawn chairs across the circle and lift weighted shade shelters off the ground.
I am convinced that there is another kind of turbulence that can be experienced both in near calm and windy conditions. Where a thermal is basically a vertical shaft of twisting and rising air that is warmer than the surrounding air, I think that there are "rollers", or horizontal shafts of air that are rolling across the ground surface. When one of these things move over our circles, models will do some strange things. On several occasions with the model in level flight, not in a maneuver, that thing will be disturbed, like go loose on the lines, turn in and show parts of the airplane I do not want to see from the center of the circle. I have not lost an airplane from this, but on one occasion recently, there was a short lived doubt a recovery could be made.
Keith