Jailbreaking makes the iPhone a geek-oriented device? Excuse me? Apple hates it when you jailbreak because it means no revenue from the App Store. They certainly don't want you stepping outside their pretty little barred garden.
WP7 looks to be pushed by MS in the same fashion, and if anything iOS and WP7 devices will be the first to apply whatever punitive lockdown measures are available.
Kinda sad how so many people seem to be rooting for extremely locked down systems for what is arguably the next tier of personal computing.