I don't think that you can assume that "anyone with a little tech ability" is a large chunk of the marketplace. Most of the people at my work don't know what is going on when their email stops syncing, and rely on me to get it working again. It is a very, very simple thing that I show each person how to do, but they always forget or don't care and log another job next time it happens. These are the people that make up the vast majority of the market. They want something that will just do what they want it to do. If they plug it into their pc to sync their files and it suggests a free software update then maybe they'll do it, but I cannot see them rooting their phone, finding an updated rom and installing it, that is completely beyond them.
For technical people I can see Android being open as a bit of a plus, sure. But if you're sufficiently technical you can jailbreak your phone and do whatever you want to it, too. As far as I can see here in Oz carriers don't bar jailbroken phones, you just have to be more careful about updates that come directly from Apple. The worst that can happen is that you have to restore your phone to an official version of iOS and start over. You are also barred from using the app store on your phone, but if you've jailbroken it then there are ways around that, and in fact it's probably assumed that one of the reasons why you're jailbreaking your phone in the first place is so that you can load media on & off in the way that you wish, rather than having to go through iTunes.