I ended up getting a VPS account from tummy.com running Ubuntu breezy (with plans to migrate to dapper when tummy.com has support for it).
Sean Reifschneider of tummy.com (who for anyone who has attended PyCon should know since he keeps the wireless running every year which is no small feat considering the typical bad connection we have provided to us) emailed me last week answering my questions about what it takes to set up Apache with the proper mod_rewrite rules to get the sub-domain stuff working the way I want it to. I also talked to some friends of mine and they all said that it wouldn't be too difficult to get up and going, especially since this stuff should only require setup once and then I should be able to just let it run (this is open source, right? These servers are supposed to be robust enough to have amazing up-times =) .
My current plan is to figure out how I want to handle DNS, get my new domain pointing to the right place, get Roundup running, get Apache to forward to Roundup as I want, and then start developing my personal site on Django.