ITunes Match Started Working?!

Question

I realize we probably aren't supposed to complain about things working but all of a sudden in the last two weeks iTunes Match has started working for me.  Like a lot of users I had constant problems with Match constantly getting stuck on Stage 2 or 3 and the process just never seemed to work or finish successfully.  I had signed out and signed back into Match more than a dozen times.  But out of nowhere it started working on OS X (Mavericks) every time.
Not sure if it's related but I went through and purged a bunch of songs and videos as well as all of the apps I had stored on iTunes from the early days of iOS.
Who knows what triggered it and I'll probably jinx myself.

Answer 1

Right, I think we're getting there, but I must warn you that this probably isn't going to be all that easy, and I haven't had recent experience with using two Apple ID's within iTunes, so my advice may not be absolutely correct.
If I understand correctly, you have one Apple ID that you have previously made App purchases with, and then another that you have used for iTunes match. Do you use the new one for anything else?
Your problem is basically caused by your using a different Apple ID for match. If you had used your old ID then it would all work fine. However, I am a little concerned about any solution using the two.
As I say, I haven't had experience with this, but I imagine that the problem is caused by the fact that Apps will only update if you are signed in with that ID, whilst Match will only work when you are signed in with that one.
One solution that you will probably not like, but would work, would be to write off the iTunes Match subscription you have made and re subscribe using your old ID. You would of course also have to rematch your library. I'm not recommending it, but it's an option. It would at least resolve the issue once and for all.
You could keep on logging in with each account to update Apps, but I think that would get very messy.
I am a bit concerned with the situation regarding your iPhone and iPad. I have heard of issues where people have found them blocked from match for a period due to changing Apple ID's. I don't know exactly what causes it. It would be a shame if you couldn't use Match on those devices though.
I don't think I'm going to be much more help really, but at least I think we have got to the bottom of what your problem is. Hopefully someone else on here may be able to give some better solutions.