20-24 oz. for the tranny: don't recommend the synth for the primary unless you change out the friction (fiber) plates of the clutch. The fibers soaked the old oil and the synth may cause slippage because it can't displace the old.
16 oz. (half quart) on an '89 - period. And yes, it MUST be perfectly upright to read the stick and I agree about NOT using synthetic (anything) in the primary. Friction discs won't like it at all. I recommend not using gear oil either.
I'll stand down since I don't own one. Only worked on FLT's and FXR's and they do have the same internals but different transmission case according to the parts book. (I just looked)