The HST housing does see a small amount of internal pressure. The HST has 5 relief valves. One of them, the case relief valve (part 22 on attached), vents case pressure into the mid case. The WSM does not give a pressure setting for it, but says "it opens and flows the oil directly to the transmission case, so that the oil may not leak against the sealings". This indicates a low relief pressure - to keep the HST free-flowing internally with little resistance.
One of the "sealings" the valve protects is the gasket that failed and now needs replacing. The WSM doesn't state the relief pressure or how to test it - but the valve should be checked for easy opening function. With wear the HST's normal internal component leak-by can increase in volume. With higher flow, a sticky or restricted relief valve could contribute to gasket or seal leakage.
In jhiller18405's case (post 2), the leaking gasket repair needed reworking twice - implicating not just insufficient gasket strength, but maybe a wear-related increase in operating pressure inside the case? Does your HST perform normally other than the oil leak? Dick B.