I'm a mobile QA guy and work with both platforms - I needed a rooted Galaxy S2, since Android (even as of ICS) still doesn't respect the proxy setting properly for apps (so I need a requires-root app called 'Autoproxy' which lets me intercept and modify HTTP requests, I use it to inject error conditions and such).
I have to say that at least in terms of the end-user tools, rooting an Android device is *much* more difficult than jailbreaking iOS. Also there's the fact that on iOS I don't need to do any of that, I can just use a stock phone and it'll send everything to the proxy defined in the wifi settings.
Obviously personal preferences differ, but based on what I've seen of Android from working with it every day, and the things that annoy me about it vs. the things that annoy me about iOS, at least for the moment I'd never choose Android for my personal phone or recommend it to friends who ask what to get.. (although I'm constantly re-evaluating that as we get new 'gifts' from the project manager, it's just that Android has never won so far..)