A few years ago I helped my mum pick her first pair of 'proper' IEMS, as she kept buying cheap Sony ones that kept falling apart and got fed up... which is where I reeled her into HeadFi land. Picked UM1s as they were just about in the price range she was willing to spend and comfort was v. important, and she seemed happy with them and her old Creative player (she's no audio nerd though). Anyway, after being jealous of my iPhone love and her newish laptop not playing nice with it, she's replaced her ropey old player with a 4G 32GB Touch and I spent this afternoon showing her how to use the thing/iTunes/apps e.t.c. Heart-warming stuff I tells ya.
Obviously now she's upgraded everything else, she's thinking about keeping the UM1s just for the gym and upgrading to something nicer for home/holidays. I'm thinking something midish-range, probably dual BA. She mostly listens to contemporary chart music, 80's stuff (power ballads, Genesis, Mike Oldfield, Fleetwood Mac e.t.c.), lot of female vocals and last time I looked most of it is fairly low bitrate, although I need to re-rip a load of stuff for her as she had a lot of things in .wma, so I can improve things on that front, and hopefully if she buys more stuff off iTunes it'll be in 320 AAC.
I realise that things have come on quite a way from a few years back in terms of SQ p/$ but there's just a ridiculous amount of choice now so it's hard trying to decide. I'd add that she'll likely buy them while they're over in the States on holiday this summer so we can ignore UK prices. I've had a look at a few of the uber-exhaustive lists of IEMs which has helped a bit, but it's still a proving a bit of a headache. I'm guessing $250 would be an absolute max since I seem to remember ordering the UM1s from the US and getting them pretty cheap compared to the £90 they are now here, and there's that disconnect between the size of IEMs and the price which she still hasn't quite overcome (although the stupidly thin Touch is helping her address that).
Any ideas appreciated!