[AmberShah]

This is good advice, and I think that's what went wrong in this case. We were told to estimate based on what we had, even though we needed to go deeper. The rationale was that we couldn't put so much time into a proposal that was so small. And on a smaller project, more risk was acceptable, which is okay, I guess, but then this is what happens.

"Setup development environment: 40 hours"

This is ridiculous, though, well UNLESS you are hiring someone to pick up work on a large existing project, in which case they may actually need the time to get all the dependencies and get it running. To be clear, our items are always in chunks of actual functionality, because this makes the most sense to ... well, everyone. And it makes it easier for them to pick and choose/set priorities/etc.