I can not answer for large sites (nor for makesite.py specifically), but in general to your scenario, yes, all pages would need to be regenerated. I guess you could think of it as a build server. But instead of building code for an app that you would be deploying, you are generating your content for your static site/blog. That being said, you could then create a build server optimized to generate your content, and/or try a static site generator whose forte is the build/generation process (I think hugo fans tend to highlight this feature for that platform?). Maybe instead of generating all content on your local machine, you could keep all your content on a beefier machine, and generate it from there - which could process stuff much faster, etc. Even still, it is probably unlikely that one would have to alter things like sidebars or footers that often, right? Also, worse case scenario, something tells me that even if needing to regenerate that many pages, i mean, would it be ok if it takes just a few minutes - probably not the end of the world, right? (I guess it depends on the timeliness of the single post or footer change that needs to wait for 100,000 pages to get regenerated, eh?) I hope my comments helped a little.