I have a Mac and a Vista machine. I bought the Sony 505 and had it for about 3 months before the Kindle came out. I found the Sony store software slow and buggy and finally gave up on it.
When the Kindle was finally back in stock I ordered one and have not picked my Sony up since. I love how you can wire connect it to the Mac and it pops up on the desktop like a drive so you can move books over to it.
The whispernet is very nice when you want to order from Amazon and the selection there is much better than the Sony store.
I'd say just download and install stuff on your Mac to the Kindle by wire, and download from Whispernet at times when you are in areas where you can do that.
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