I believe this is partly due to long term relationships aspect of the IPO process.
During roadshows, underwriters are essentially leveraging their rolodexes. These relationships constitute a significant part of the value they are bringing to the table.
If there would be a different price for each investor, some would get a better price than others, and those that got a worse price would not feel very good about it, likely deeming it unfair (there are still people behind the processes, and people can't help but experience emotions of fairness and a lack thereof).
As a result, relationships would likely suffer due to this human aspect to it, and weirdly enough, these grudges can easily get absorbed in the 'institutional memory' and linger there long after the original human protagonists have left the organisation.
A way to address this, would be to introduce rules like first-come-first served, which would imply giving up a degree of control by underwriters and the company. This, however, introduces risk for the company which, after all needs that control in order to maximise value.
It's not a simple problem to solve, but maybe there is a better solution somewhere out there...