The foliage on 'Oakleaf' is beautiful and I'd love to try it someday. I've experimented with the species for years, yet to produce a passable bonsai, but I've come close a couple times. Take these observations for what they are worth.
Let the plant grow wildly until the trunk thickens enough. I usually prune once a year in the late spring for rough shape, then not again until the following spring.
Root over rock is so easy with this species. You have the aesthetic advantage of using the rock to compensate for a thin trunk.
Try an interspecies tanuki. This is my latest project. I killed my best bald cypress and could not bear to throw away the corpse. I carved some channels in it and planted several cuttings at the nebari. I am training the cuttings up the channels then away from the trunk to form branches. Obviously this will never create an illusion like a juniper tanuki might. I'm going for the look of a massive dead tree taken over by vines. Right now this is in the "grow wildly" stage so it looks like a green Cousin It. This spring I will prune it drastically to see what I've got, then let it run rampant for another season.