I'm not saying I support all of Warren's plans on higher education - canceling student debt entirely and making tuition entirely free both seem like stupid moves to me as well. College should be affordable enough that it's a viable life choice also for people from disadvantaged backgrounds - but making things entirely free tends to make people rather careless about them, which you really don't want with something as important as higher education.
But I do think that some steps need to be taken to make college more financially affordable for new students, as well as for existing graduates who still struggle with the debt. Not only for their own sake, but also for the sake of the nation as a whole, which will also benefit from college being affordable for a wider group of people.
And as a general point, the argument of 'I did things the hard way, so now if you make it easier for the people coming behind me, that's unfair to me' is understandable enough, it's obviously a natural reaction, but if you allow that to become the deciding argument, it can block almost any kind of change, including more conservative priorities:
- you want to lower taxes on high earners? People who just retired from high-paying jobs, or who passed on a promotion/job change because it would be a lot more stress for a minimal net wage gain on account of a higher tax bracket, will be cursing you.
- you want to reduce regulations in a certain sector? Fat lot of good that'll do to the people who just gave up their businesses in that sector, saw them go bankrupt, missed major opportunities, etc. on account of those regulations. Or even if they did thrive in spite of those regulations, they still had to put a lot of effort and money into complying with them - now you're screwing them over by letting new entrants in the sector skip all that.