I'm sure you're 100% right on staged payments, but my question is "does it matter?"
We won't receive a cheque up front for £75m for VVD, but were we to sign, say, Theo Walcott for £30m, we wouldn't be expected to pay that up front either. Our outgoings would be staged in the same way as our transfer income.
On the history, Osvaldo and Ramirez were obviously very bad misfires, but on aggregate we seem to have been very smart on the transfer market, with the good acquisitions easily outweighing the bad ones.