But then once you've told us, unlike a normal human bookkeeper, we won't forget about it later — we'll actually encode a rule in our software that will enforce this check going forward.
(And yes, you also do benefit from "If our system has seen this type of transaction somewhere else, we can make a more intelligent guess")
Are you telling me that it gets automatically tagged as marketing? Because that seems... naive at best, and hugely problematic at worst (as it can result in a huge amount of expenses getting incorrectly tagged).
(Every outsourced bookkeeper today has this challenge, and there are a variety of options for resolving it, depending on what the customer requires.)
Rules cannot be applied to these transactions. For the obvious ones, I already have automatic rules build right into QuickBooks Online.
What is different here?
I use Wave, which lets you upload receipts and it will perform OCR to extract vendor info, date, total cost. It's not much of a leap to go 1 step further and look at the line items and categorize...again just a guess.
Suppose User A has a bank entry "Payment to Stormy Daniels" and classifies it as "Hush Money".
User B also has a bank account entry "Payment to Stormy Daniels". Will the system suggest to User B that the entry should be classified as "Hush Money"?
Generally speaking we like to take on the work of the "monthly close" — i.e. making sure the books reflect what happened in your business the previous month, and we're less keen on doing stuff like following up with your customers who haven't paid, both because (1) that's something you probably want to have happen more than once a month, and (2) there's actually a lot of on-the-ground knowledge that you or the sales rep have that we may not have.