I got some feedback on my FreeBSD dilema. Kief left this in my comments:
Russ, BSD isn't all that hard to get your head around if you already know Linux, especially if you've had some experience with other Unices as well. Each flavor of Unix has its slight differences, but most of the differences come when you use GUI sysadmin tools from the commercial vendors (Sun, HP, etc.) - at the shell/configuration file level they're pretty similar. BSD in particular is about as standard as Unix gets, it is derived directly from one of the original versions of Unix, and hasn't had the odd proprietary add-ons of the commercial brands. John Companies' service sounds like the dogs bollocks, if I didn't already have a colocated Solaris box I'd seriously consider them. I've also used Verio, they're decent, but they won't let you install your own servlet engine at that kind of price level.
Posted by kief
And Darren posted his endorsement for FreeBSD on his site:
If you know Linux, FreeBSD should be simple to pick up. I use FreeBSD at home for all the things I don't need windows for: my CVS repository, email, web surfing, mucking about with perl, python, scheme etc. I prefer it to Linux - it seems more solid somehow. The filesystem layout tends to be more consistent too, mostly due to the packages/ports collection mechanism. I haven't taken the plunge with Java on it yet though.
Thanks guys! I still haven't gotten that page fixed, and it's the beginning of the month, so it might be a good time to think about switching for real.