The last early Ford 3 speed transmission that I assembled (50 pu, top loader, w/open drive) the counter shaft had such a neat/tight fit in the case, that I doubt much, if any gear oil will leak out of that area.
* Also, some years ago I purchased a new cluster gear counter shaft and new caged roller bearings for this cluster/counter shaft assembly, and during assembly of these parts in the transmission I determined the shaft and the rollers on the bearings were both undersize. These new parts came from a well known dealer/supplier. I was lucky to catch this problem before final assembly. My point is....check and double check your parts very carefully, whether they are used, new/repro, NOS, or otherwise.