>What is the external pressure on you or the dean or university to make things easier for these people?

Mostly that students are all giant piggybanks that spit out tuition every year. And, from experience, a lot of administrators view themselves as doing a service for marginalized students (who are often more likely to come in ill prepared and wash out like this). They are generally old and paternalistic (and sometimes a bit racist) and often just assume that all such students need lowered standards rather than what they actually need (a kick in the pants and plenty of resources to help them get their shit together).