There are a lot of reasons why enterprise software sucks.
The largest reason is because companies see it as an IT issue. When it comes time to select software to purchase most departments will not invest the time of their best people. The people who can most easily be spared for the amount of time involved are put on selection committees. Users don't see selection as an investment in the future but as work that doesn't help them today. So in answer to Jason's basic point: users don't select enterprise software because they don't see selection as an important use of their time.
The next largest reason enterprise software sucks is because people don't want to change. They want new software to work the same as old software so they don't have to learn anything new. It is the main reasons why there is so much customization work. Its a combination of people being lazy and managers not wanting short term efficiency ratings effected.
The largest reason is because companies see it as an IT issue. When it comes time to select software to purchase most departments will not invest the time of their best people. The people who can most easily be spared for the amount of time involved are put on selection committees. Users don't see selection as an investment in the future but as work that doesn't help them today. So in answer to Jason's basic point: users don't select enterprise software because they don't see selection as an important use of their time.
The next largest reason enterprise software sucks is because people don't want to change. They want new software to work the same as old software so they don't have to learn anything new. It is the main reasons why there is so much customization work. Its a combination of people being lazy and managers not wanting short term efficiency ratings effected.