First, there’s more to his arguments than not having to remember things. You have to compare written knowledge to oral tradition. If you read something and have questions, the words aren’t going to magically change to something understandable. If you are learning from someone and have questions, you can ask that someone and they can rephrase it in a new way that’s easier to understand. In a similar vein, if you read something written long ago like Shakespeare the language will have changed such that it’s more difficult to understand. If his stories had been passed down by word of mouth the meaning could be kept while the words used to communicate those meanings evolve with the language. Of course writing has many benefits that make it worthwhile, but pretending that the only argument against it is that it stores information on a page instead of your brain is wrong.

Second, people calling a new thing bad in the past has zero relevance to people calling a different new thing bad in the present. Plato/Socrates had no word generating machines in their time, so what do their opinions have to do with a word generating machine?