No tricks. Same methods would apply like the others you have done.
Was the old o ring still in the groove on below the splines? Perhaps it had rotted and is still up in the bottom of the crank?
Only put grease on the splines, NOT on the top of the driveshaft.
I shift the motor into FWD gear, that gets the upper shift rod up and out of the way for now.
Ensure you put new grease on the splines, the water tube, and around the inside edge of the water tube grommet on the impeller housing. This ensures it slides in smoothly, and does not bind, causing water restriction.
Shift the gearcase into Reverse.
Slide the gearcase up, align the water tube into grommet, and slide up. If it stops before the halves mate, rotate prop CCW (youre in reverse), while pushing up. It should slide up that last half inch when the splines engage. Put a bolt in to hold it. Then, through the access panel, pull the lower shift rod up into Neutral, and shift the upper shift rod down into Neutral. Ensure the detent is lined up perfectly in the hole, then install the bolt. Test all the gears. If you are happy, install the remaining bolts and you are done.
Other thoughts:
Your 1956 15hp had a trouble spot. The lower crank seal is a weak spot. If it has not been changed, it is likely shot. They get so bad that they fall apart. This allows water into the powerhead. Obviously bad. It may have fallen apart, and a chunk of it keeping the drive shaft from engaging? Seems unlikely that it could get up in there, but who knows. Regardless, while you are it this, I would change the seal if you have not already.