See I'm teetering on the edge of the whole iPhone thing.
My issues, really.
1. I used to have a smart phone (okay it was crap), but... I only use the phone function rarely - so when I need to use the phone, I need it to be really simple, because I don't spend enough time on the phone for me to learn the nuances. The smart phone I had was a pain (like Mr Clam said, take the phone away from your ear, get the number pad up, hit 1) - it just wasn't a good phone. At the end of the day, when I make or get a call, I need to be able to use the thing as well as I can my simple Nokia (or any simple basic phone).
2. There's a benefit to having an iPhone, called "mass appeal". It means that essentially, if you need an attachment, or a an app - because it's so popular, there are dozens to choose from. It makes getting car adapters (I have one for my head unit which allows me to control my iPod from the steering controls) and just "stuff" really easy. I've found with the Nokia smartphones we have here, and the old Windows mobile phones we had - it's all a bit of a nightmare. With the iPhone, everything is popular and therefore easy.
3. Not overly convinced by Apple mobile products to be honest. My iPod crashes fairly regularly. You also hear a lot of people with a lot of problems - but again, popularity means that you hear about more horror stories (Apple suffering from PC syndrome
).
Erm, really, it's the phone issue that is causing me concern. I have a choice of Blackberry too which will do pretty much as much, then keep my iPod as a separate device, but I'd like to have a single device really. So I don't really know at the moment, but the biggest issue is that you you just don't know until you've spent a week living with these things (preferably three weeks for the novelty value to wear off). However, the number of positive testimonials by "ordinary people" (not tech geeks) does tend to really show in the favour of the device.