you can crack an iPhone and do custom setups. i haven't bothered as there's a fair bit you can do without jailbreaking it. plenty of apps to make your own ringtones too if that's what you're after. there's apps for just about anything...
I don't have an iPhone, but the girl has a pad, so same shit. It's definately nice enough to use, and because I don't use it much, I probably didn't really grasp the problems with itunes/ios restrictiveness, until she asked me to put some ebooks on it for her.
On my Android tab (and phone) I just copy the files from the PC to the folder I want them in on the device, or email them to myself and download them. Then pick my ereader app of choice (often depends on file type), select the file and presto, I'm reading.
Want to do it on the ipad? Well forget drag and drop. First of all you need to add it to your itunes library, then sync your ipad with that computer. That alone caused all sorts of issues with books purchased from the itunes store not wanting to transfer onto the computer properly, which was stupid enough. Eventually though, the files were on the ipad, and opened up in ibooks. Problem was, the formatting was a bit funky in ibooks, so she wanted to try them in an alternative app.
"No worries" I think, just start downloading apps, open the file and see what it looks like. Not fucking likely! Despite the fact that the epub is obviously stored on the ipad somewhere because ibooks can read it, it doesn't actually exist as a file that another app can access. To do that, you need to download it to the ipad specifically for the other app! You need to duplicate the same file, in the same format, just so that it can be accessed by different apps!
That is bloody rediculous.