Allo, qeeksquadofun! I support my 79 year old mother's reading too...from Toronto to Montreal. The trick is to put the books into a shared Dropbox once I have "fixed" them for her and then have her follow the step by step instructions for adding them to Calibre (I did print screens of each step with play-by-play text for each). Adding them to her reader is not that difficult for her with the "manual" but asking her to edit Metadata or Convert is just too much, sooo...I add books for her from time to time after I've fixed them and since she's got a fair number to read until the next time I have time to add more, everyone's happy!