I had a similar problem recently. Redid the brakes. Everything new or rebuilt. On rear, two new hubs, new drums, rebuilt backing plates etc. Hubs were bought 4 months apart. When I went to reassemble, one hub slid on easily. The other would not go on. It started to slide on and then would stop, but would rotate. I checked everything. Tried reversing the hubs (even though they were not arced to the shoes) just to see where the problem was. Sure enough, the hub that slid on easily slid on on either side. The one that would not go on would not go on either side. I completely removed everything except the backing plate and axle. Same result. I measured the hub race - right on spec for a new one. I measured the axle race, a little wear but still within tolerance. I checked the bearing - meets spec. Called Bratton's, they shipped a new drum and hub that they verified would mount correctly. (Love their customer service!). The new hub would not go on either. The same exact problem.
Now the hub would start to slip on the axle (no axle key by the way), and then appear to bind as the bearing starts onto the race. Yet the bearing fits beautifully on the axle and spins freely, and fits beautifully inside the hub and spins freely. But when mounting, it binds. If you force it a bit (with a big hammer), you can see where the rollers are leaving a slight score line on the axle race.
Yet everything measures correctly - or at least as close as I can tell. I finally borrowed a stock of rear bearings from the local supplier and checked them one by one. Five bearings would not work. With the 6th bearing, the hub slid on wonderfully. I removed the bearing to measure it to see how it is different than the others. I cannot find any difference in size. Anyway, I surrendered! At least the car went back together correctly and without force, but I still wonder why it would not work with 5 different rear bearings ( a mix of old and new but all serviceable.)
Good Luck on figuring it out.