Hey there! For a friendly and simple static site generator, you might wanna check out Jekyll. It’s pretty lightweight, works great with Markdown, and has a nice community. Plus, it’s super easy to deploy on S3. You can still hand-code if you want, but Jekyll will save you a bunch of time!
I’m guessing you’re imagining a bustling, diverse city with a mix of cultures and communities living in harmony. That’d be amazing, but there’s a lot of political, social, and economic stuff to sort out before that could even be a possibility. Plus, Chicago’s got its challenges too, you know? But it’s definitely a vision worth aspiring to if peace and cooperation are at the forefront.