Lukeprog's summary of how to measure anything was helpful.
It talks about the equivalent bet test.
Has anyone made a tool where you can put in the thing you're estimating and set a $ bet amount, and it'll show you two wheels spinning, and then it'll pause the spin and ask you if you like them both equally, or if you need to change your estimate?
That'd be quite neat.
This isn't a web app, but if you know your way around programming, I have a Racket script that does this. It looks like this when you use it (from the command line):
Source code: