I need some advice

So Jason and I are up for an upgrade on our cell phones.  And of course, I work amongst Apple lovers who all worship (in the non-sacreligious sense, of course) the iPhone.  Heck, even my mom has one.  And I'd be lying if I said I didn't think they were cool and would love to have one.
However, I'm not 100% sold.  First hindrance is, of course, the cost-and not just the cost of the phone but what it adds to our monthly bill for the data and texting plan.  Second hindrance is its size.  My current phone is less than half the size of the iPhone and fits easily in my pocket.  It's especially important that I keep my phone with me on work days in case the kids' school needs to contact me.  Right now I stick it in my pocket in the morning and I'm good to go.  Everyone that I work with has to carry it around everywhere and only put it in their pocket if they're standing.  It always seems like they're fooling with it (and leaving it somewhere).  Plus, if I'm always carrying it, then I'm for sure going to be dropping it, meaning I'd need the insurance, adding to the cost!
Also, I currently do not have internet access on my phone.  I have been in a handful of situations where it would have been helpful to have access to my email, or contacts, or google maps while out and about, but not so many that I feel it's vital to my next two years.  If I got an iPhone, would I use that feature enough to warrant the extra expense?  Also, I'm slightly concerned about how connected I currently am.  Would the iPhone just make it worse?  I feel like everyone just sits in meetings staring at their phone or compulsively checking it. I don't want to be that person.
I guess my issue is that of course it'd be completely cool to have one.  However, money doesn't exactly grow on trees here in the Russell yard.  And frankly, I'd go back to my very first 10 pound Nokia rather than give up my cleaning service.  But on the other hand, if I don't get one now, I'll have to wait 2 more years before I can get one without breaking my contract.
Am I totally stupid to not get one?  Is there like a second best cool phone that would give me more functionality than I currently have (an absolute must is some type of keyboard-still texting with T9 over here!), but not add so much to my monthly bill?
I hate the whole 2 year thing.  And ours always seems to come up for renewal at a terrible time-I feel like this time next year would be better for us to bite off the finances for it.
Anyway, your thoughts on being part of the iPhone family or your thoughts on NOT being part of the iPhone family are greatly appreciated!