I work with ColdFusion every day, and it's the scripting language I first took to on the web after I graduated from college. I've loved it like my own. Like everyone has said - CF9 is coming out soon, as is CFBuilder - both extremely exciting events for the ColdFusion community. But I feel like all the things that made the language great - it's ability to rapidly and easily build sites, the community which was so strong before, it's lightweight pick-me-up feel, are slowing and steadily being sucked out of it in favor of more 'enterprisey' concepts. It's certainly not outdated now, but it's trying its damndest to become so.
The state of the CF community is pretty fractured right now: Of the people who are vocal, the guys who blog and talk about this, it seems like there is a great divide: on one side are the OO purists who feel that OO is the savior of everything and the coolest thing to come along since sliced bread. On the other side are the people who favor the old-school procedural approach and think that OO in ColdFusion is silly and inefficient (partly true) and that OO is some newfangled kids' toy. And then there's everyone else, who is stuck in the trenches working with these concepts every day, just trying to write the best apps they can. A lot of very smart people who grew up with the language have since moved on - the OO/Procedural evangelicals are the ones who've stayed. However, the people who have stuck around are extremely passionate.
It feels more and more that ColdFusion is being used by Adobe as a strategic way to push the Flex platform. It seems, to me, that it is falling by the wayside, even with all the great changes being brought about in CF9. It's still competitive and it's hanging on, but it's got a feeling about it that it knows it's on its way out. Adobe claims that people are continuously adopting it, but the general attitude seems to be that Adobe is full of shit in that regard.
However, to really answer your question, it becoming ever more outdated doesn't make it any harder or less enjoyable to use. I also want to reiterate that it's having trouble keeping current - it doesn't mean it's a currently outdated technology. It's also still the easiest and cleanest language when it comes to connecting to a database, running a query and manipulating the results.