Manosound,
For lack of anyone with more experience chiming in, let me offer a few things you might try:
1. Grind just a bit more chamfer on the ends of the driven gear teeth and file between them a little bit to ease it's way into the drive gear.
2. Grind a bit of chamfer on the end that goes into the bush beyond the drive gear so as to ease its entry therein.
3. Check to see if the new drive gear has the same O.D. as the original on the end that goes into the bush beyond the drive gear. If not, maybe, chuck it up in a drill motor and hold a file against is to slightly reduce the O.D.
4. Don't be stupid and forget that the lay shaft turns when in neutral, making it easy to turn the rear wheel and get the teeth in line.
5. While tapping the long bush home, keep turning the rear wheel in the forward direction (of course this will be harder in fourth gear than neutral, if you happen to forget).
6. When close to home, slide in the keeper screw and tap the bush in or out, as necessary, while pushing on the keeper screw so that it can find the relief in the bush.
I don't know if any of these will work, but good luck.
Richard L.