The desire for syncing everything seems to point to iOS devices (e.g. iPad and iPod or iPhone). However, they don't have SD cards.
The Motorola Xoom seems to have an SD card, but I don't know about syncing with other Android devices/apps.
I think you'll be hard pressed to find a Device #2 with a radio. Most devices with a radio that I have seen are simple MP3 players. Unless you mean internet radio.
Not sure what you mean by "Must be able to use it as a phone (act as the base, not the handset!)".
There are a few 5" tablets, I think, like the Dell Streak phone, that might be ok for Device #2, other than the comments above.
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