Neck is too tight
Virgin case .498 Fired case .4995 sized case .499 Case neck absolutely will NOT accept a bullet. All my current guns and every one I've ever had would easily accept a bullet just as you described.
Worker,
In regards to the neck. Take a fired piece of brass. A bullet should go in and out of the neck with no resistance. If it drags at all or it is a very very close fit your necks are too thick. In regards to the body if you had a 1" micrometer you could measure a virgin piece of brass just ahead of the extractor groove and compare that with a fired case and a sized case. If there is a problem with chamber dimensions that is how you diagnose it.
If your chamber is too tight have your smith polish out the chamber. I have reamers that just a tad too tight and do it frequently. It's no big deal if you know what you're doing.
Virgin case .498 Fired case .4995 sized case .499 Case neck absolutely will NOT accept a bullet. All my current guns and every one I've ever had would easily accept a bullet just as you described.