I started reloading back in the mid 80s, back then, I was a mere private and could just barely afford the Lee presses and dies. But being military, military surplus ammo was always my go-to since it was about the cheapest you could find. So I have always loaded military brass, and but for only a few instances, it has always reloaded just fine. As a matter of fact, the only time I had an issue was when I started converting 5.56 brass into 300BLK, and now 277WLV. Maybe it was because I never ended up with any cases fired from MGs, or any weapons with loose chambers until then, but even now I don't own any SB dies. What I do now is full length size the case, then turn the case 1/4 turn and size again until it falls into the Sheridan case gauge, usually twice but sometimes 3 times.
I have used a few different case lubes, the Lee, Hornady One Shot, RCBS Imperial and a DIY, and for the most part they performed well. When I started messing with converting cases, I had a few stuck cases. I at first blamed the lube (one shot) as they were really stuck. But now I think it was a combination of a small rim and a loose Lee shell holder that were more to blame. Now that I am more solvent, I decided to "upgrade" all my dies and have gone to RCBS for the most part (not much of an upgrade IMO), so it was only natural to get RCBS shell holders too, and I find that they are tighter around the rim, making more contact with the case. I also feel that the Lee dies, at least mine, are looser as well, because the Hornady dies I now use to form 300BLK seldom need more than one forming/sizing operation. So when I converted over 1k cases into 277WLV, I didn't have one stuck case using the imperial, RCBS case holder, Hornady die combo. The cases may not have been shot from MGs though, so it may not be a fair comparison, but so far so good.