Well after holding out forever, I've finally made the plunge to Community Server. There are probably still some quirks, but so far it has gone pretty well. I moved everything between servers using the DotText-CS-Converter tool created by Kevin Harder. I had to spend some time reworking the tool so that it would work with 2.0 and so far it seems like my tweaking worked.
Let me know if you see any issues. Thanks!
Update: Seems the update broke the main feed so I used a redirect page to fix it. However, it also broke the category RSS feeds and I can't think of an easy way to fix it since the format isn't your typical format (/blog/category/xx.aspx/rss).
Anyhow, besides those two issues and the fact that the galleries didn't get migrated it seems that everything else is working.