I know what you mean; the high school production of Hairspray that I did in February (which was in Theatre 2, below) had 22 wireless mics on stage.
My situation is like this:
Theatre 1: have a couple IEM systems that the MD owns. We'll be on stage (doing Chicago, ironically). They run the actors through it and keyboards (since they don't use amps), with a couple of personal monitors for drums and horn players. Hearing myself isn't an issue; the PJB stuff shines in a pit environment in that I can turn it up and it's not boomy but still has the definition. So, I can keep the amp at a level that I can hear it and the soundguy still has control over the FOH and the stage.
The current IEM that he has are the earpieces that have the foam inserts. They never stay in. I used a pair of $20 Sony on-ear headphones for half of the run last year (3.5 weeks, 6 shows a week) and they worked alright. Not ideal or comfortable, but they stayed put as I was switching between electric and upright.
Theatre 2: They run a click track. The click track is the only thing going into the headphones. They have really crappy headphones that we use. Again, no need to hear myself through the monitors, or anyone else. The entire pit (which is usually 20+) is in a separate room, all mic'd and DI'd.
In both situations, instruments (aside from keyboards) will more than likely not be in the monitors; just voices or a click track. The need for ambient sounds from around me is therefore extremely important. Wearing one earbud in and one out isn't something I like doing, mainly because it's uncomfortable for me.
So, that's where my initial question of "is there really a difference between the really nice consumer earbuds (which are really IEMs but marketed differently) and the actual professional IEMs" came into play, because for my situation, I can't really see a difference. Nothing will be completely isolated and run through the monitors, just vocals at one place and a click track at the other. I will still need to hear ambient sounds, because many of the other instruments with me will not be run through the IEMs, just a mic for FOH (if they need it).