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The Apple lossless format should be the same sound quality. It also supports metadata, like artist name, genre, song title, etc. to my knowledge wav does not. Also, if an iphone/ipod user downloads a new song they will have immediate access to it. If you're using a memory card you'll have to bring it in the house and update it.
It doesn't sound like you're in the Apple "ecosystem". If you were using itunes to buy and manage your music it would be much easier. You don't have to think or care about formats etc. it's pretty easy to rip your CDs into itunes also.
It sounds like you have an existing digital music collection that's not in Apple format, so I can understand your frustration. I remember being frustrated with itunes at first too, but it's pretty good once you get used to it.
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