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iTunes Match Help Needed

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I have a small number of old iTunes purchases that I'd like to upgrade to 256kbps from 128. It's been a while, but I guess iTunes Plus is no longer available, so you have to use iTunes Match if I want to do this for multiple tracks. If anyone can provide some guidance to the following questions, I'd really appreciate it:

(1) It really is a small number of tracks that it may just be cheaper to repurcahse the DRM-free/256k versions. How do I do that? Delete the existing tracks and try to repurchase within iTunes?

(2) If I went with iTunes Match to upgrade these tracks (and I know that there are many threads/webpages that explain this), will I still be able to keep the upgraded tracks if I let my iTunes Match account expire after a year? Or will they stay upgraded only if I keep the account active.

(3) I have a number of CDs that I have put into iTunes, and many are missing artwork. I was planning to use software such as TuneUp to clean up my library. Does anyone know whether iTunes Match meses up with how TuneUp works, particularly artwork? I've read some posts that iTunes Match causes problems with artwork.

(4) OK - Completely dumb question: How, exactly, do your iDevices access the music stored by Apple in its cloud service? If it's via cellular data or wifi, that would be crazy because of data costs. Is it just a way of syncing without actually connecting to physically to my Mac laptop where my iTunes library resides, or something else?

Many thanks in advance.

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