About the mockup, I wonder why not indenting the destop options?
Something like:
│ [*] Debian desktop environment
│ ... [*] Xfce desktop environment
│ ... [ ] GNOME desktop environment
│ ... [ ] KDE desktop environment
│ [ ] web server
or
│ [*] Debian desktop environment
│ └─ [*] Xfce desktop environment
│ └─ [ ] GNOME desktop environment
│ └─ [ ] KDE desktop environment
│ [ ] web server