I have two piercings in each ear, one at 8ga and the other at 12ga.  The 12ga are new--just a week or two old.

The 12ga I've had for years, and have been stretching them.  The 12ga are the ones giving me problems.  They were initially pierced with a gun at the mall.

18->16 went smoothy, and wasn't even really a stretch since I've always worn heavier earrings.
16->14, about a month later, was rough.  I didn't use a taper or anything, I just put the next size of jewelry in.  It resisted, and bled a little bit.
14->12 was worse.  I had about two months from 14 to 12.

12->10 was ok.  I used a stainless steel taper lubed with Neosporin, and this was about two months after going to 12ga.

10->8 went smoothly, I used acrylic tapers lubed with jojoba oil.

I was going to post pics of my ears a few days ago and ask if I had catbutt ears, but my camera wasn't working and now I know I do.  It doesn't look that bad, but that might just be because 8ga still isn't very big.  But the catbutt isn't what I'm worried about primarily. 

Also, for the 10ga, and 8ga, I've been wearing claws and plugs, both of which have those little rubber o-rings.  Sometimes the o-ring on the back of my right ear goes inside of my piercing and then I have to fish it out--which hurts and brings out all kinds of gunk (usually because I don't realize it's in there until it's in there for a few days).  Could I have had a blow-out and not known about it?

Last night my silicone o-rings went up inside the piercing while I was sleeping.  I woke up...groggily, and fished the o-ring out clumsily, and took the claw rings out of my ears, figuring I'd leave them naked few today to heal up.  When I woke up all the way I went to the bathroom and noticed my right ear was a mess of dried blood.  I cleaned it up, and I haven't had any bleeding since, although my ear is swollen up pretty good (I can't even get anything in it) so I took 3 ibuprofen to help with the sweeling and I brought some H2Ocean to work to use throughout the day.

So, after establishing some context my questions:

1.) Is it possible to have a blow out and now know it?  I'm a little worried I might have had a blow-out in my right ear, because the o-rings keep going inside the piercing.  It's probably something to do with healing or a small blow-out. I'm not sure what it is.
2.) Is the catbutt repairable, and if so, how do I fix it?  I'd rather avoid downsizing if possible--but will if that's the only way.  I'm at an 8ga right now, and I'd like to stay at least at a 12ga or 10ga if downsizing is an absolute necessity.
3.) If the catbutt isn't repaired (or isn't repairable), then will it get worse if I continue to gauge?  I'm fine with how my ears look now (assuming I don't have a blowout--which I don't *think* I do) in regards to the catbutt, but if they're going to get worse then I might just let them seal back up and not bother with it anymore.
4.) Is wearing claw earrings bad?  I heard it is awhile ago, but can't seem to remember where I heard it.  It might have been here.  I've been wearing claws because the plugs have to have the o-rings right up against my ears, which feels weird.  I think I might have an allergy to the rubber o-rings--I seem to do better with the silicone ones (although the silicone ones still got up in the piercing).

EDIT:

I know better than to not use tapers, and will be using steel tapers in the future.  So that's one conversation we don't need to have.Also, the last stretch was textbook.  No bleeding, no swelling or pain.  Just nice and easy.  Last stretch was around the end of July, and aside from the catbutt (which I think I've had since I started stretching since those first few were done wrong) and the o-rings going in I haven't had any problems since the last stretch.

 In regards to your last comment, you don't need to use tapers. It's best if you've waited long enough that the next size can just slide in (called dead stretching), although it doesn't appear that you waited long enough between any of your stretches for this to happen. Some people also prefer to tape rather than taper, since it allows for a more gradual stretch. See:

http://forums.bodyartforms.com/forums/t/5641.aspx  AND

http://forums.bodyartforms.com/forums/t/24279.aspx

In regards to your specific questions:

1) People can have all kinds of things and not know it; the short answer would be yes, it's possible. Is there a flap or ring of extra skin around the back (or front) of your ear? To me, the fact that o-rings are going into the fistula indicates that your jewelry is too short.

2) The newer the catbutt is the more likely it is to be repairable. You should downsize as much as possible (i.e. take all your jewelry out, not just go down a size). When your ears aren't irritated or pissed off you should begin massaging them with oil; my preference is emu oil. This will help break up some of the scar tissue.

3) Yes, it will get worse if you continue to stretch. "Gauge" refers to measurement.

4) Avoid hanging designs or heavy jewelry is fresh piercings. You want to stick with some simple, single or no-flare, glass or metal (titanium or stainless steel) plugs. The claws add too much uneven weight and can lead to uneven stretching. Also, they have the tendency to get caught on things much more than "normal" plugs. Switch to silicone o-rings if you think you might be sensitive to the nitrile ones (duh).

Hope this helps!

Claws aren't necessarily bad.  However, they are only made to be worn in well healed (not freshly pierced/stretched, not irritated) piercings for short periods of time.  Wearing them to sleep isn't such a great idea since they can get knocked around, which may be why your ears were swollen and bleeding.

As Jellybean said,your best bet would be to downsize your ears as much as possible to let them heal up for a while.

I  tried the tape, and I really hate the way tape feels in my ears.  I think I'll stick to tapering, and just give it extra time from now on.

1.) Nope, at least I don't think so.  There is some scabbing and stuff right now so it's hard to tell.
2.) Ok. I'll leave them naked for maybe a week, and check on it after that?  I've got jojoba oil, will that work?  I don't have any emu oil.
3.) Whoopsie in terminology.  I think the catbutt is old, so it might not be fixable.  Figures.  I do the first few stretches wrong and then when I start knowing better it might be too late. =/
4.) I can't wear plugs because they're too short for my ears, but I can't wear hanging stuff because they hang uneven.  So...is there a special kind of plug I can wear or something?

 You need to downsize for months, not a week. Seriously, of course you don't want to, but it's necessary to give your ears a chance to heal. How thick are your lobes, because there's some jewelry out there with fairly long wearables...

I was planning on downsizing for longer than a week, lol. 
I said I'd go without wearing anything for a week and then see where I'm at if I'm ready to put jewelry back in.

How far should I downsize, 10ga, 12ga? 
And my lobes are pretty thick I guess, I never thought about it.

Would CBRs be okay to wear?

jebbewocky:

Would CBRs be okay to wear?

Sounds like a good idea for you since you've been having so many issues with o-rings.

What kind of plugs have you been wearing?

It would be best for your ears to downsize all the way to 12g and it is ok to wear CBRs.

I've been wearing basic stainless steel no-flare plugs.

I'll wait a week, see where I'm at, if I'm good to wear again, I'll put in 12ga CBRs, and see how they are in a year.  I'm getting married next year and don't want unsightly ears!  I have a perfectly good pair of 12ga CBRs that I've never used, because I can't even get the beads out of the ring.  Maybe I'll buy some pliers?  Or would it be easier to just buy a new set of CBRs?

Get some pliers.

These have been working well for me =)

Maybe next paycheck.  I also have two other 12ga CBRs...except I lost one of the beads. =/

I know we can buy the beads by themselves here, but ordering just a bead seems like a bit of a waste on shipping.

 I'm confused, and maybe I missed something, but isn't the ear that's causing trouble at 12g now? In which case, you should be downsizing smaller than 12g, preferably removing jewelry altogether...in which case you don't need the 12g CBRs or an extra bead.

I think the OP is currently at 8g, but they're downsizing to 12g. (Please correct me if I'm wrong)

 Precisely. I replied earlier on, but it doesn't show for some reason.

jebbewocky:

I have two piercings in each ear, one at 8ga and the other at 12ga.  The 12ga are new--just a week or two old.

The 12ga I've had for years, and have been stretching them.  The 12ga are the ones giving me problems.  They were initially pierced with a gun at the mall.

jebbewocky:

Also, for the 10ga, and 8ga, I've been wearing claws and plugs

I've read it over and over and I'm just not seeing it. I'm glad it makes sense to everyone else, though.