I didn't stay in VIP, but visited friends in VIP several times. I have to say, Bonnaroo finally has the VIP thing down. I went VIP a couple of years ago and the only thing worthy of VIP was the location. This year, the VIP tent area was fantastic and the VIP viewing area for What was top notch. If the bands are good next year, I'm definitely going VIP.
Many small improvements that were smart. the VIP stage / tent / music was about 1000 times better.
the free food / party on thursday was well organized. free beer was a bit of a fiasco - long lines. but what do you expect
i overheard one technician talking to someone on a walkie talking about piping in the video/audio feed from the main stage into the VIP AC tent next year.
the bathroom attendants must have been told to not outright harass people for tips since they were all much more subtle about it. my gf overheard one of them talking about making about $80 in tips one afternoon - and she was pretty stoked about it. im guessing if your job is to clean toilets at an outdoor rock concert, you probably arent making tons of cash - so every little bit helps.
I thought VIP was much improved over our last time in 07 even without the food. Thursday night was great and the A/C bathrooms were consistently clean and cool! I really liked the hill over the bleachers of the past. Well worth it!
You don't anymore (or didn't have to this year). You could buy a single GA ticket, then purchase an upgrade to VIP through a company that was on bonnaroo.com...it was tailored to people who flew in and wanted the VIP experience, and it included the round-trip shuttle.