This thread is fantastic with a lot of great resources! I have a related question but I don't want to start a new Ask HN for it. I have been using Machato app

This thread is fantastic with a lot of great resources! I have a related question but I don't want to start a new Ask HN for it. I have been using Machato app on Mac (https://news.ycombinator.com/item?id=35471091 https://news.ycombinator.com/item?id=35471091) for the last few months. This is a very nice app but with limited functionality. For example, it doesn't allow uploading PDF documents and asking questions on them as described in so many responses in this thread. I tried to search for a Mac app with this capability but my search came up empty. All the results I got are for web apps. Has anyone come across such an app? Paid/free doesn't matter.