Yip read the upgrade docs and white papers .I wouldn't say it is pretty painless , cause I have experienced majour hasles with sql 6.5 to sql 2000 . What...
Just a tip never use auto shrink , cause you will not know when SQL will shrink the database , it is actually recommended by microsoft that auto shrink...
Why don't you run a profiler trace on the stored procedures that the web app is executing , maybe you will find something there . Also look at your stored...