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I rewrote an invoicing system (originally in .NET) in Python and yeah, I totally feel this. All the system did was generate a CSV file that could be input into another system (Quickbooks, iirc). The original .NET version was nonsensical at times, replete with bugs, and I spent a lot of time trying to figure out what the original intent was (there were no docs, of course, and finance often had conflicting/incorrect ideas about what the system should do.) Version 1 had to simply replicate the csv generated by the original system exactly, which required purposefully writing some bugs that I discovered along the way.

But yeah, there were all sorts of nasty complexities -- this was a usage based system, but there were (optional) tiers (pay less for higher tiers), as well as certain time segments that were discounted. And then there were cases where multiple accounts could share a set of data and get a discounted rate and/or only one of the accounts would be billed. And on and on....

One lesson I drew from this experience was that, when discussing things with finance to try to figure out what the requirements were, it really helped to have pictures. I would create these elaborate usage/time graphs, and color in portions to reflect different billing/pricing scenarios. These made it much easier to discuss the current/future behavior of the system. Because saying "really, this is simply the integral of a usage function over time" didn't fly.




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