opkg list-upgradable shows nothing at all, which is a bit concerning. If it has run I'd rather it said "Nothing is upgradable" or similar than looking as if it hasn't actually run.
Clearing the browser history fixed the web-if problem, I can now see the advanced packages list both for installed and available and NTP client is installed and doesn't need an upgrade. I then went back to the standard list of packages and again I had to clear the brower history before that actually worked and showed the shorter list. Something is definitely broken somewhere, is web-if correctly quoting all its pages as not cacheable?
I would check that your Internet Explorer Options settings (General Tab, Browsing History, Settings) are set to check for new versions of stored pages every time you visit the webpage. On the Foxsat firmware they used to issue that advice for IE users but they eventually solved it by making nothing served by the web server cacheable at all (not something I'm massively keen on doing). I haven't seen many comments posted about the T2 custom firmware a caching problems, but this is a setting you might want to check.