Homebrewer,
Always keep the immortal words of Charlie Papazzian in mind. "Relax. Don't worry. And have a homebrew."
OK. Here's your first issue:
Homebrewer said:
Well, I measured about 10 cases and most were between 1.580" and 1.582". A few were around 1.576" However, I didn't trim them because they are all below the trim to length of 1.585".
No.
Here's the SAAMI drawing of the .357 Magnum. The cases should measure 1.270" to 1.290". Trim-to is normally in the middle of that at 1.280". So I think you have been looking at data for a .357 Maximum, which has a case that is 1.585"-1.605", with trim-to length being 1.595" nominally.
Whichever cartridge it actually is, the cases getting shorter means you've been shooting it at low pressure. Pistol cases tend to shorten if you use them at pressures below about 30,000 psi. That's because they don't stick to the chamber at lower pressures, instead backing up into the breechface and swelling to fill the chamber, which makes them shorter and fatter. They never quite recover their length completely during resizing from that shape, so they get shorter.
Whichever cartridge it actually is, the COL irregularity and the ability to push the bullets into the case are related. When a case is not adequately narrowed during resizing, the grip it gets on the bullet is likewise inadequate. When you seat the bullet you are probably lowering the press ram immediately afterward, and the air you just compressed in the case can then push the bullet out some. If the case is tight it holds on. If it is extra loose, the air bleeds out and the bullet also stays put. There is a magic range within which the bullet is pushed back out. Try raising the ram and leaving it there for ten seconds or so to see if giving the compressed air some time to leak out at least reduces the problem.
Why are your cases failing to get snug enough? I've seen this in .45 auto cases. It's always been in cases with the R-P headstamp. They just made the brass near the mouth too thin, so as it work-hardens from repeated sizing, it is able to spring back from the resizing operation. The same thing is perfectly possible with other brands with thin necks. I'm just saying that R-P is where I saw it before, and .45 Auto is where I had bullets seem to levitate partially out of the case due to compressed air and before I got them to the crimping station.
There are two cures for the above in addition to giving the air time to bleed out. One is to replace the brass. That's probably not a bad idea anyway since you know they are short and you want to start loading full-house, which old cases won't withstand a lot of anyway. Starline makes both .357 Magnum and Maximum and their brass that I've had (.45 Auto, .38 Special, .357 Mag, 44 Special, 44 Mag) has all been of the best quality currently available. I recommend you get some of their brass specifically, even if it is just a small quantity to try (Midway and Midsouth both sell the brand, and you can buy direct from Starline for larger quantities). If the new brass works, you'll know the brass was the problem, and that will mean I was proved right a your expense. That's my favorite way of being proved right; someone else footing the bill.
The other solution is to buy a smaller diameter sizing die. Lee sizing dies that I have tend to err on the wide side of the range, presumably to avoid wearing out your brass prematurely. They should work fine with Starline brass. However, you can buy a Dillon sizing die and it will likely be smaller. That same .45 Auto brass that would not size properly in either a Lyman or a Lee or a Bonanza die, sizes just fine in a Dillon die. I think this is because the Dillon is made for a progressive press, and you can't have some cases working and not others in a progressive loading operation or you get unusable ammunition mixed in with good ammunition and everyone is getting mad at you and blaming your machine instead of the brass.
Hope this helps.