Went over all your pics you posted. That primer hole tool is your issue. here is a pic of the reamer I have next to a primer. Get one of these and your fixed. Get that tool I told you to get. These come with it.

I ordered the Lyman tool.  That puts me over $100 just in additional tools to fix this primer issue.  I really hope it helps.

It should. Sent you a pm to get your address so I can send a few ready to prime brass. PM me your address. Don't need them back. Heck, if the tool doesn't work, I'll drive down myself and get you going! Use my brass for comparison.

I just replied to the PMs.  I appreciate all of the help you guys have provided.

The Lyman tool came in today.  Looks like I wasn't adequately reaming the pockets, because after running the Lyman reamer through them I had no further issues.  I also took the primers out of the cases I felt were too buggered up to shoot.  I'd like to get your opinions on these, and whether they would have been safe to fire as loaded ammo.  They all have a mushroom head on them from being squished by the press.  Only a few show signs of damage along the sides.  The anvil separated from most of them while decapping, though I'm not sure if that was a result of the trauma on them or just from depriming to begin with.  I've got 100 rounds loaded up right now with primers that are similar to this run, though not as extreme as these.  I would hate to have to pull down 75+ rounds or however many have buggered primers, but I would also hate to disassemble my rifle (or my face) because the ammo is unsafe.  What are your opinions here?

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150418_201559.jpg

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150418_201612.jpg

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150418_201724.jpg

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150418_201804.jpg

Trash them and move on.

Obviously these are no good, I was more looking for opinions on if the other loaded ammo that may have primers in a similar condition would be safe to fire.

Wow, those are mashed even worse than my first efforts, and I trashed mine.  I've deprimed a few mashed live primers using a 5/32" pin punch IIRC.  I wore safety glasses, gloves and hearing protection, but none went off.  At that point I learned how to better prep pockets  as well as controlled primer seating depth and 'crush'.

BE VERY CAREFUL punching out live primers.

There are two members here on this Forum that are wearing primers under the skin from depriming live primers.

Fire them first in your rifle.

Soaking in water or oil will not reliably kill them (as I found out the hard way = BANG)

bbqncigars, are you back in IA, or that other un-loved state?

My rifle is still out of commission due to that broken extractor.  I hydraulically removed about a dozen of them, but it wasn't kind to the case mouths.  I am aware of the danger of depriming live primers.  I soaked them in water first which got a few of them (water stained yellow when I poured it out) but the rest I was just REALLY careful with.  I used my normal resizing/decapping die with the punch.  I figured this would be the safest way to do it if the primer went off.  The die would contain the cartridge, and the primer would shoot down through the base and out the bottom of the machine.  

As for shooting ammo with primers like that-- what's the verdict?  Obviously less than ideal, but can it be reasonably considered safe, or should I pull down a BUNCH of loaded ammo?

I have shot my bad primers with no ill effects. Just went outside and loaded 1 at a time and shot.

I went through my loaded ammo and pulled out the ones that I wasn't 100% confident in.  I came up with 28 total.  None of them are as bad as the rejects that I already deprimed prior to loading (hence why these got loaded) however, these show signs of flattening on the primer, some don't sit flush with the base of the case, and some show signs of brass loss.  

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150419_170810.jpg

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150419_170800.jpg

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150419_170738.jpg

http://i37.photobucket.com/albums/e86/ibdmentd/Mobile%20Uploads/IMG_20150419_170729.jpg

These are fully loaded rounds.  FMJ bullet, and 212gr of WC860 powder.  What I need advice on is if these are safe to fire as fully loaded ammo, or should I pull the bullet and remove/replace the primer?

After viewing your most recent pictures, I feel your cases have too much deformation left over from the military crimp to allow the primers to fully seat.
Also the priming punch is too small allowing outside of primer to not be supported by the punch. I use a 3/8" diameter dowel pin (flat end) to final seat the primer and flatten it. It will need mounting to a shell holder to hold in proper alignment. A 3/8" dowel fits perfectly up thru a RCBS shell holder, however the lead angle may need to increased slightly.

I don't know about the rest of you but I would NOT shoot them. Pull them. To much a risk. Better safe than sorry.

Your problem is the lee priming tool. Your primer pockets are probably OK.

The priming post has a spring loaded primer holding cup with a chamfer to allow easy placement in the primer holding cup. Nice Idea. BUT!

When you start to push the primer info the brass pocket, It starts to encounter resistance. That chamfer allows the primer cup to expand outwards and cause the trouble. How to cure it?

Take the Lee priming post and primer cup holder and shorten the cup until 90% of the original chamfer is gone. The primer cup Has no where to expand to.

Priming technique. Bring the priming ram up to the brass. Rotate the brass. You will feel the primer centered in the pocket. Prime with one solid stroke.

Keep away from the mouth of brass for obvious reasons. I have never set off a primer but there is always a first time.

I load around 2000 rds a year. This works.

Could you post a picture of your priming setup?  I'm having trouble picturing it.

I am out of town til this weekend. Will pm you then.

Interesting about the Lee Classic cast press with the 50BMG set-up. I cant speak for all of the other people with the same set-up from Lee. But I have reloaded over 500 rounds without problems. And yes all of my brass were at one time one time fired with primer crimps. Its all about primer pocket prep. And knowing what it feels like to push in the primer and how much pressure to use to set or arm the primer.

I never have an issue with my Lee press provided the primer pockets are cleaned correctly. Lee designed it for a reason, being spring loaded. Helps maintain primer until it gets to the socket. Has never interfered with the primer.