> Am I naive for thinking that nothing like that should take as long as 6-9 months in the happy case and that it's absurd for it to not succeed at all?
Bluntly, yes. And so is every other reply to you that says "no this isn't naive", or "there's no reason this project shouldn't have finished". All that means is that you've not seen a truly "enterprise" codebase that may be bringing in tons of business value, but whose internals are a true human centipede of bad practices and organic tendrils of doing things the wrong way.
> whose internals are a true human centipede of bad practices and organic tendrils of doing things the wrong way
Currently there. On one hand: lot of old code which looks horrible (the "just put comments there in case we need it later" pattern is everywhere). Hidden scripts and ETL tasks on forgotten servers, "API" (or more often files sent to some FTP) used by one or two clients but it's been working for more than a decade so no changing that.
On the other: it feels like doing archeology, learning why things are how they are (politics, priority changes over the years). And when you finally ship something helping the business with an easier to use UI you know the effort was not for nothing.
Bluntly, yes. And so is every other reply to you that says "no this isn't naive", or "there's no reason this project shouldn't have finished". All that means is that you've not seen a truly "enterprise" codebase that may be bringing in tons of business value, but whose internals are a true human centipede of bad practices and organic tendrils of doing things the wrong way.