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That's exactly what I do (my parents) for the same reasons. Of course you could just email them the books if you wanted to avoid the calibre complications. My Mum won't touch a computer unless someone has it all set up for her and down to a few simple clicks/key presses. My Dad is more adventurous but still not always technically inclined enough to get there on his own. So while I was visiting I installed calibre with an initial setup and showed him the basics.
Now he does all the book importing from a dropbox folder I top up for them from time to time with just the MOBI versions. I helped him setup some custom columns to track which books he and Mum have read. He started off with one library and using user categories to divide books for Mum and him, but since then decided that he just wanted separate libraries for each of them which is what he has now. The Kindles are setup with the Kindle Collections plugin (being the Kindle 3 Keyboard versions), and he does the loading onto the Kindles for both of them. We setup a specially named "_Reading" collection that they put books into as they read them, and a "_Read" collection for when they finish until they next get back to the computer, record it in there and remove it from the Kindle. Mum even printed out and laminated a card she tucks into her Kindle cover behind the Kindle giving her the instructions on how to add a book to the _Reading collection and a few other basic things to help her out with the device (she is not very patient with technology without some simple instructions to hand).
Both of them are total addicts now, take their Kindles everywhere and haven't gone to the physical library since they got them. And Mum has recently apparently started looking at the books in calibre every now and then to see all the covers and descriptions which she enjoys. I would like to setup a web server for them so she could just use a web browser to do her casual browsing rather than battling with Dad to get time on the main PC, but it might be easier to setup one for myself here and let her browse that over the internet. We shall see...
They have convinced a number of their friends to get Kindles now too so it has definitely been one of my more successful experiments. Good luck!
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