See my other thread about semi automatic copying to Kindle.
https://www.mobileread.com/forums/showthread.php?t=72467
My idea was to print or copy everything during the day to c:\kindle and then one click to sync out to Kindle and take it home.
I see you have a DX so this is probably going to work better for you than it does for me. If I print to pdf from an average Word doc then I get a A4 size pdf and eye strain on the Kindle 2. I have to resize my Word doc to A5 and then print to pdf.
Wishing I had the DX now