Important points are interactivity with popular data sharing and productivity software. Part of the reason AmigaOS feels so dated is that its nearly impossible to share, produce or consume data used by other operating systems in an easy manner.
Examples of this are opening, modifying and creating spreadsheets, current video formats (MP4, H.264, FLV, Silverlight, etc..), current audio formats (OGG, MP3 (with good playback), FLAC, FLA, etc..) word documents, open type documents, hell even RTF documents.
We can't really go to most websites which is a huge source of communication these days, you can't consume YouTube or half the time even visit email sites due to a lack of a decent browser; at least not without a serious sacrifice in productivity and usability.
Things like YouTube and GMail seem trivial given the things you can do with AmigaOS but these are the medium through which much communication happens. Even if you get your news form news.google.com or TheVerge or reddit or any of those other sites, we barely support JavaScript and most browsers on the Amiga have no CSS capability at all, let alone the CSS used on current/modern sites.
So long story short, if you can perform your daily routine with only that one operating system and still partake in sharing, consuming and being productive with current data formats then you are likely using a modern OS.