[allenu]

I've had similar experiences on many projects. You start out thinking something is going to be super simple and you provide estimates that match your naive design and later find it'll take 2.5x-5x longer than you wanted. It's definitely humbling.

Nowadays when I have new work that has a lot of unknowns, I try to jump in and create a proof of concept as quickly as I can, even if it requires a ton of hacks. I want to know right off the bat if there's something obvious that's going to make the task take much longer than I wanted.