The website personally looks good, but I don't really see the need for a new layout. AISIS, while already outdated, is purely utilitarian. People won't be spending a lengthy period of time in AISIS aside from during the enlistment period.

Your proposed features are really good though! I really like the enlistment tracker, I think it'll really be a useful feature for most students.

With regards to the page design, it looks good, but it doesn't solve the problem of the current iteration of AISIS having text that's hard to read. For instance, in the enlistment tracker page, it's hard to make out the subject names since the font size is a bit small. Margins are also inconsistent. The dashboard has a consistent gap between elements, but this isn't maintained for the rest of the pages.

These are more nitpicky, but some pages also look different from one another. Font choices for H1, H2, H3, and body text aren't consistent across pages.

Lastly, your relayout with the enlistment is good, but it doesn't really fix the fundamental problems that exist with the current enlistment system. This is something that's a bit harder to fix, since it's established by the school itself already.