Thanks for the responses.
Yes, I was going to give each client who was interested in making Bitcoin payments their own address to send to. Maybe I was reading wrong, but it seemed like it was recommended to generate a new address for each transaction
and that's where the confusion came from (as I can think of no way that one address per transaction would be any easier to keep track of than one per client account).
I still have a ways to go convincing the powers that be that this idea is on the up and up - grey area isn't really good enough. It seems like the accusations of money laundering and whatnot haven't really hit Bitcoin, and that if they did it would really only apply to the people operating exchanges, but I still want to make sure I don't open us up to any legal issues as we don't have the time/resources to deal with them. Perhaps I'm being paranoid in the non-traditional sense.
So far I feel like if we only accept Bitcoin for accounts who we have legitimate account information for, and who have already made at least one "traditional" payment, then we can't really be accused of doing anything grey-area. It probably goes against the philosophy of Bitcoin by being reliant on other payment methods, but until I've sought legal advice I only really want to dip my toes in, so to speak.
Edit: Wish I'd seen this thread
first, now I look like a chump.