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Me and a couple friends “hacked” our school back in ~2002, so this would be really realistic. One of us came up with a reason to get the teacher to type in the library password, I was in charge of distraction, and a third shoulder-surfed the password (it was “media” spelled backwars, aidem). Just goes to show it doesn’t have to be anything super complex.

2005 predates BackTrack linux (precursor to Kali) and the MS08-067 vuln (discovered in… 2008!) so if you want something showy that is also realistic… well, I’m sure there’s something from that era, but you may as well go with one of those and you’d be in the right era.

Edit: It looks like MS04-031 might be a good target if the system was unpatched (which wouldn’t be far fetched at all), it’s got a metasploit module. I’ve never actually tried to exploit that, but maybe a modern version of Kali with some legacy/vintage theme and a WHAX wallpaper?