I've been having a heck of a time working with MediaTemple's DV service. The way they've set it up, the apache user cannot write to upload/month/day.
You have to be an experienced system administrator to figure out this problem.
MediaTemple suggests switching from Apache to FastCGI module. They have instructions to do so as well, but I have yet to find any concrete examples of how to do this with WordPress on a live environment, without risk.
Anyone moving to MediaTemple DV should be aware of this issue, and hopefully the WordPress folks can help to solve it, because it has eaten up over 50 hours of my time just researching it and trying to figure out what to do about it.
That is horrific usability.