You can hook a hose barb to a grease gun (⅛" pipe thread) and attach a suitably sized hose which you stick down in the sump with the plunger fully depressed. Stick it in, pull out the plunger, bring out your oil.....they make them commercially so converting an old,unused grease gun is a no brainer.
Most gearboxes run on half full or less especially on things like ring gears (differentials) where the ring dips in a shallow sump and distributes the oil all over the place....case in point where is the fill plug on your vehicle differential.
On the ½" Pipe plug, go to your auto parts store and get a venting plug and insure you install it vertical....I think your description says your current plug is mounted vertically. Venting takes the pressure off the gearbox when it gets warm and this goes a long way in helping to keep oil in old gearboxes with worn out blade shaft seals.