That's what I do - calibre is fairly straight forward, you can import all your books into your calibre library, send them to your reader, remove them from your reader and give them tags so you can sort them. That's pretty much all I do and I worked that out without too much effort.
Just make sure you get books in epub or lrf (sony format) wherever possible as they don't need any converting. If you're using a 505 you can ask a question in the 505 forum and people help as much as they can
