Since the well of things I actually cared enough about to part with Bitcoins over appeared to dry up, I decided to go ahead and pick up some NameCoins on the BitParking exchange, and register a few NameCoin domains.
NameCoin still doesn't work on FreeBSD - I can't manage to build a working binary and my linux_base has too old a libg++ for it to work, so I went ahead and set it up on a Debian VM to get things going.
Once I had it up and running, it didn't take long at all to download the blockchain (stark contrast to Bitcoin proper, which seems to take an eternity), and before long I was up and registered with a few domains. The name_firstupdate command takes a bit to actually show up in the blockchain (12 confirmations after name_new) but it doesn't take long with merged mining blowing up.
The downside is that as yet, there's not much in the way of usability for NameCoin domains. The only two public nameservers advertised on the Wiki both appear to be broken, the public whois service appears to be broken (despite the webserver on it advertising otherwise).
I thought about setting up my own DNS server, but so far all the scripts I can find to do it involve weird PHP hackery to scrape the entire domain space and create bind zones for each one. I don't really think I'm prepared to descend to that level of hackery, and I suspect that's why the public nameservers are busted.
I'm thinking about writing my own DNS server for it in Python, with a caching bind server in front of it (only public for .bit domains) but I'm not sure if I'll get around to doing it or not. It sounds like a fun project, but I've got so many projects going as it is.
I'd also considered setting up a .bit registrar, simply because it seems like once I've done this there won't be too much work involved in it - but I am not entirely sure how to secure it. It seems like the whole system relies on having the private keys on a box someplace, and I don't particularly like the idea of a system where one box gets rooted and every domain you've ever registered can be taken.