Have wrestled with this problem many times over the years--and not just with handloads.
Once owned a Remington 700 .300 Winchester Magnum that wouldn't chamber even factory ammo easily--and some rounds not at all, including Remington. Eventually ended up lapping the locking lugs enough to solve the problem.
Somebody mentioned this earlier, but "painting" a case with a Magic Marker and then chambering (or attempting to chamber) the round will often reveal the problem area.
Have also more than occasionally encountered FL loading dies that did NOT match up well with the rifle's chamber....
