To each his own, guys.
Some people don't have the large vials and stirplates needed to get an adequate cell count in a reasonable number of steps.
Also, unless you're preparing your starter wort in an AUTOCLAVE or pressure cooker, and pitching a totally pure yeast culture, with immaculate sanitary practice, it is going to be slightly contaminated with bacteria/wild yeasts. Wort is almost always going to have a little bit of these contaminants, but ideally the cell counts are small enough to be manageable. And each time you step up the starter, you are also increasing these cell counts, thereby increasing chances of the contamination turning into an infection.
And of course, each time you step it up, you're also further exposing it to external contaminants.
And the last reason I can think of, off the top of my head, is time. Some people don't want to or just can't wait that long for a starter. Considering how long a single step takes to ferment and crash cool in order to decant, it's not unthinkable that somebody might be brewing frequently enough to need to have 3-4 stirplate starters going at once (instead of quite a few more simple starters!), but simply don't have the equipment or capacity to do so.
So there are certainly reasons for wanting to use multiple vials with a starter - it's all about the balance between costs and benefits, and everybody is obviously going to balance these things differently.
Me? I never buy multiple vials of the same yeast to pitch in the same beer.
But I can still recognize it's a valid practice. If it wasn't a valid practice, I don't think Jamil Z would set up the MrMalty calculator to be able to tell you that, for instance, you need to pitch 3 vials into a 3L stirplate starter. Heck, my Brewzor Android app even includes the ability to calculate a multi-vial starter with multiple step ups.
However, even though it's a valid practice, it's NEVER a necessary one, and so saying that you NEED to use multiple vials if pitching into wort above a given OG is incorrect. And personally, I find yeast expensive enough that I would never recommend - a stirplate is definitely a worthwhile investment, and a 5L E-flask is also a purchase I'd make again in a heartbeat.