Is a static site gen right for me?

What if I want more functionality with my blog in the future, back-end and more interactivity. Is that possible with Ruby and Jekyll?

(Disclaimer) Unfortunately I have Windows and not confident running Jekyll, so I’m wondering about static site generators in general. I have been looking at Hexo and Node in particular, and if someone can address the limitations of static-site generators in general that would be helpful.

The answer can only be “that depends”.
And it will depend on just what you need.
While Jekyll is a static site generator, it does not prevent you from adding php scripts server side, nor will it prevent java script client side.

In general running interactive services means that you will have a lot more trouble in site maintenance (A LOT!). Unless you use interactivity providers like etc.