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As someone who lives in both worlds, Apple and PC, the most frustrating area is the lack of flexibility in Apple products. In all fairness to Apple, their goal is simplicity. iTunes is a perfect example. For many people it is a fabulous program for handling their music and books.
However, it is too simplistic for my needs. There is little to no customization possible. For example, what if you want a specific category for music that is not listed? In comparison, look at MediaMonkey. For books, it is joke - look at Calibre. You can use any type of device with either of these.
Do you need to use a USB? No - look at dropbox or another similar service.
Pick which phone you like the best. Then test iTunes and MediaMoney and Calibre. They can actually all co-exist together, but you need to learn about how to transfer information from one to another.
Good Luck.
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