Why on earth is it called an Oleo? Here's why: "Oleo" is simply an abbreviation of "oleo-pneumatic", which is a fancy way of saying that your strut has oil and air in it. (They probably did use air back in the 1940's but as your tailwheel is going to sit around in a museum for many more years than the anticipated life span of your average Barracuda, you might be better of to adopt modern practice and charge it with nitrogen).
Does the strut actually incorporate a hydraulic damping element? -If not, then strictly speaking, it isn't really an oleo at all, but a plain old pneumatic strut, which is a shame because you would then have to put all of the ladies' cosmetics-based humour on hold until you get round to the main undercarriage legs.
By the way, your second trim-tab-type-thing on the elevator is a servo tab. By moving in the opposite direction to the elevator, it works like a little elevator of its own and generates an aerodynamic force that assists the movement of the elevator, thus reducing the effort required at the control column. A clever yet simple device which you will still find in use today.
Right, that's enough smart-arseness for the time being. i'm going to try to get back to sleep now.
Obstacles are those frightful things you see when you take your eyes off your goals.