The Winchester down stroke tilts the cartridge upwards on the feeding ramp, and pushes in in on the upstroke. It should feed faultlessly no matter how slow or fast you work it. It wont go upside down though...
I have never seen a Winchester 94 that wouldn't feed properly. But I have seen one with a crooked barrel. Whether it was made that way or a horse rolled on it I don't know. I have also seen one with that wasn't quite screwed in right, the extractor wasn't quite round enough, and the sights were off kilter. I suspect it came that way. I have looked at a lot of them though.
What is more common in rifles made in the 1960's, or ones that have been used hard, is to have a loose lever, caused by the lugs not locking up tight enough. This is no big deal except I don't like rattly things and I don't like the lever dropping down when you step off a log or something. Marlins can be loose as well. It annoys me so much that I wont buy one over the internet anymore, I need to look at it.
Older ones will often show mildly pertruding primers in the cases. This is a sign of excessive headspace in this cartridge and rifle, but it is really no big deal and can be happily ignored.
The Best Winchester 94's are the pre-64 made rifles. The next best are the rifles made in the 1970's right up until they made the Angle Eject model in about 1982 or so. I have no opinion on the AE models as I have not had one.
I have never met a Winchester 92 in the traditional chamberings that wouldn't feed either.
But if the Rossi 92's in .357 or .44 mag (both cartridges the Winchester 92 was not specifically designed around) wont feed then look at your ammo - the Winchester design is not sharp angle friendly on a bullet, a Keith style bullet with a wide meplat, or a wad cutter design may not feed. And is sensitive to overall length. If it is jamming as it coming up, it often is to do with the distance between guide rails, and they can be carefully shimmed.
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