You have a lot of parts to your question, and you're somewhat vague about your skills and background, so it really isn't easy to give you a straightforward answer.
If you're a programmer - the Mirror API can handle just about any server-based programming language that you're used to. If you're familiar with Ruby - go with that. If you're familiar with something else, there are code samples (and libraries) available for Java, Python, Go, .NET, and PHP and further information for other languages if necessary. Find the language that works best for you to access the data.
Speaking of accessing the data, it isn't clear where your data comes from, so that is pretty difficult to advise you on. Although you called it a PDF, you pointed to an image file. It looks like it comes out of a spreadsheet or database. Trying to access a PDF or image will be very difficult, while getting it out of the database would be far easier using any of the languages. You should probably ask another SO question specifically focusing on this portion of the problem if you're uncertain how to approach it.
On the Glass side, you should probably become familiar with how most Glassware these days work. Most don't let you ask free-form questions from the "ok, glass" screen. Even Google makes you issue a command before doing a query! While you can leverage a menu item such as "post an update" to send the text of the query, you'll then need to handle the query text itself as part of your server.
You may want to update your question to address some of these issues - or break it up into smaller parts first, tackle those parts, and ask questions with specific problems as you encounter them.
