Current file upload limit in the assistant is set at 16MB. I would like to see it increased. I don't understand why the limit exists at all, given that we are essentially paying for token usage. In my specific case, I wanted to upload a PhD thesis, which is a PDF around 50MB. I'm guessing the limit exists to protect the users from themselves, so seeing some kind of an estimate how many tokens or dollars I would use to process the file might be helpful. A hard limit doesn't make sense, especially since it's independent of the model used.
Upload a file and perhaps see a summary of its size in tokens (or $ to process it with the selected model).