The beats-to-head-fi phenom is an interesting one indeed. In gamer's terms, imagine being introduced to MOBA's through league of legends, then trying to learn Dota 2. Your going from a watered down, ease-of-use 'noob' format to something infinitely more nuanced, unforgiving, and a huge time investment for rewards that aren't necessarily everyone's cup of tea. I think, not to offend you, but Beats and Bose are essentially the gateway drug for people with a previously undiscovered taste for good sound.
If marketing hype and style satisfy your needs, and lets face it, the majority of consumers won't bother to do some light google research, beats will certainly be enough. At cursory listen, Beats provide that immediate wow and fun factor that so easily attracts a fresh consumer. I won't lie when I first put on a pair at best buy 4 years ago I was awestruck, for a bit. In that respect we can commend Beats marketing for opening the floodgates for people who would never have known about the very huge world of headgear. I stumbled upon head-fi and other related forums from a different route (always purchased low end senn's, klipsch, UE, etc since middle school), beats were never on the radar for me. It wasn't until I started making my own money that I was ready to make a moderate investment in audio equipment. In the advent of Beats, other brands (monster included) have stepped up their game in the 'mid-fi' market, in which you're just getting your toes wet.
Compare Duncan Jones' "Moon" or Michael Bay's "Transformers." Both categorize as Sci-fi, but it's apples to oranges. Transformers is loud, flashy, and fun. I don't hesitate to say the first one was highly enjoyable in a big crowded theater. Moon on the other hand is an homage to the genre. It's a character study: elegant, slow, an acquired taste, with a huge payoff if you're patient. That's just my $.02.
Also, IEM's are perfectly safe, it's a question of how you use them. They have a bad reputation because people buy less than stellar isolating IEM's and CRANK them up to drown ambient sounds. That's like standing in front of loud-speakers to drown out Time Square. Buy a reputable pair of IEM's and some comply foam tips and you can diffuse most noise (I'm talking subway noise) pretty handily. Etymotic Hf5 are well touted as being very isolating. What you lose from an IEM though is soundstage, bass rumbles. Personally they are minor losses compared to the isolation, portability, weight, and potential clarity an IEM brings to the table. Noise cancelling just irks me and I shy away from them. Most of us on Head-fi have relatively sensitive hearing and for me that cancellation noise feels like a pressure drop and it's just unpleasant.