The 'keyhole' idea has been done before. If I remember right we used wooden oars with leather wraps on some scout gigs to do this, it is a long lever aft but it works. Equally these gigs (19') were perfectly scullable with the oar in the transom recess - shaped like a rowlock. By scullable I mean sculling with one blade through transom making figure of eights, not the rowing meaning of sculling. If you really throw your weight into it those things used to shift solo.
If you needed to 'lock' the oar in, you push the leather wrap part into the horseshoe/rowlock and it cannot lift vertically. Not a sculling position but a steering one only. Obviously you could put another wrap on the blade shaft to give a shorter lever out aft ie 2 position option.