I recommend the book "Software Estimation: Demystifying the Black Art" (2006) by Steve McConnell. Nice collection of excerpts: https://leventov.medium.com/excer

I recommend the book "Software Estimation: Demystifying the Black Art" (2006) by Steve McConnell. Nice collection of excerpts: https://leventov.medium.com/excerpts-from-software-estimation-demystifying-the-black-art-9cf80e2b9977 https://leventov.medium.com/excerpts-from-software-estimatio... There is also a short chapter on estimation tools using e.g. Monte Carlo simulations. One tip which is relevant here and that is also more or less presented in the article and probably obvious :) "TIP #65: Don't treat the output of a software estimation tool as divine revelation. Sanity-check estimation tool outputs just as you would other estimates."