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If you've already invested in iPads for your salesteam, jumping to Square will save you money from the offset. The fees for taking orders when a physical credit card are present are among the best around, and the software is easy to setup and use, and the digital receipts it creates makes bookkeeping for you and your customers much easier.
Intuit has a similar solution that can actually be cheaper, though not as slick looking.
I'm sure it can be done but I have not done it myself. You may want to check out this product:
It claims to handle orders plus wireless printing, which isn't something I thought that the iPad could do in the first place.