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Right, that was the problem I was hoping to brainstorm about. I didn't want to re-open the "add data to the transaction database" discussion (I think "add data to the block chain" is misleading, since transaction data isn't actually part of the block-header-chain or transaction-merkle-tree).
I'm still wondering if there is a way to create transactions on the web server, without talking to bitcoind, using a small-ish number of pregenerated public keys, such that each transaction is unique and competitors can't tell how many transactions belong to any particular merchant.
Pre-generating a bunch of keys works, assuming that competitors don't know the pre-generated keys (bad assumption long-term if they keys are re-used, since they could just order a bunch of stuff and note the keys used for paying).