It took me 63 days to make iTunes Match finally finish matching and uploading. Step 1: Gathering information about your iTunes library went quite smoothly. Step 2: Matching your music with songs in the iTunes Store took days and days and days and wouldn't finish without following actions. When Step 2 was finally ready, Step 3: Uploading artwork and remaining songs started quite speedy, but finally I had to use same actions as with step 2 to proceed. When there were about 1000 songs remaining in step 3, iTunes started to crash and I had to take again the same following actions.
I tried all kinds of tips in Apple Support Communities for iTunes Match including turning iTunes Match on and off and using network bandwidth limiter. None of the tips were any great help.
So, what where my actions to make iTunes Match finish? Here you go:
- I used a VPN connection. Every time iTunes step 2 or step 3 jammed, I switched VPN connection on or off, and matching or uploading started to continue again.
- After iTunes started to crash, I started up Mac in a safe mode. In a safe mode iTunes Match seemed to work extremely well even without a VPN connection switching and iTunes match finally finished without a single crash.
So, after all, all the problems with iTunes Match matching and uploading were probably caused by some other application, but I haven't figure out which one. Anyway, now iTunes Match has finally finished and is complete and ready to go. Great!