Recovery Mode can reportedly be initiated wirelessly via RecBoot in iOS 5.0b2, says 9to5Mac.
You not only can sync your media wirelessly in iOS 5, but it appears you can enter Recovery Mode using 'RecBoot, Etc' from the Mac.
Unfortunately, to perform a jailbreak one must place their iDevice into DFU mode so its unlikely that the Dev Team will be able to use this to create a wireless jailbreak tool.
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- Posted using my iPhone 4