Last week at the PASS Community Summit, I was so busy that I did not get a chance to blog about anything. Looking back, I had a great time and learned a few things. In one of the keynotes, I heard MSFT say that the upgrade experience from 2005 to 2008 would be seemless. When I repeated this information to a few other MSFT folks, I got a chuckle. This combined with my experiences and dialogues with friends, colleagues, and other MVPs has led me to this point. SQL 2005 to 2008 upgrade will "seem" less like an upgrade after going through the 2000 to 2005 upgrade.
With so many installations of SQL Server 2000 still out there, the customers are asking for an easier upgrade. I was very happy when I saw the Upgrade Advisor tool for 2005. I think it helped many customers in preparing for this revolution to the current generation of DB engines. I know that MSFT will have tools available for the 2008 upgrade as well. Just as there was more work to go from 6.5 to 70 and less from 7.0 to 2000 typically, there was more work going from 2000 to 2005 than there will be going from 2005 to 2008. Your mileage may vary.