Yeah, on average the userbase has really died out and the caking on of random shit plugins didn't help.
I had planned a few events, such as enabling 'buying' resources to build with at a low price using Essentials' buy/sell commands. I never bothered because there weren't many people around for me to pitch it to.
The fireworks display I did earlier this year brought a decent turnout, though.
Adding different chats for roleplay/etc wouldn't be that hard, although it might become weird for CraftIRC. Though, honestly it doesn't seem like there's enough people to actually *utilize* such a thing.
I'm hoping that doing this and taking everyone's suggestions into consideration will help bring people to the server. It's sort of a shame to have something running that hardly gets used.
One thing I've been tempted to do is to post the server on one of those public server listings, but confine new users to a 'new people only' creative/survival map until they prove themselves.
The issue with that? No one likes an entry barrier. However, the regular users don't feel like getting griefed and then having to wait to get their stuff rolled back.