[crossi]

You don't need to go to the library for a lot of classic books. Amazon itself has a lot of free ones, also the Gutenberg site has a lot of free public domain books that can be downloaded as mobi(kindle) books. There are a bucnch of other sites that have free public domain books as most classics are that you can download in the format of your choice.

The basic functions of Calibre like adding books to your library and sending them to your device are very easy. Converting formats of non-DRM'd books is also simple. Books from a library will almost certainly have DRM and Calibre alone will not be able to convert them. There are plug-ins to do that but I would not use that for library books.

If you haven't used ereaders before I would recommend one of the Kindles. Amazon will let you return it within a month if it turns out you don't like reading on it. It gives you a chance to see if you like reading that way and you can get your money back if you don't. I'm betting you will like them a lot.