Coming from a Windows background, I would never upgrade and OS (if Windows)
I did an in place upgrade of Leopard to Snow Leopard and used migration assistant to restore a TM backup.
Then for the hell of it, i did a fresh install of SL and just manually copied files and some settings back.
Benchmarking them in terms of boot time etc. yielded no difference. So i started to believe that the upgrade route had no disadvantages.
But,
Having upgraded from 10.6.7 to Lion DP2 then DP 3, i have had nothing but problems. Slow boot times, generally unstableness, and system freezes.
I bit the bullet last week and wiped my HDD. Then installed SL onto a small partition and downloaded DP2. Ran that and selected a large empty partition on the disk ,effectively doing a fresh install of DP2. Ran all the updates and ended up at Dp3, then reinstalled all apps and just copied data from my TM backup.
Now the system runs faster, feels more snappy and most importantly has only frozen once.
So, in my experience, a fresh install of the developer previews is best...