I just did drag and drop from explorer and had no problem. I also can do a synch and it copies whatever I drop into the synch playlist. Not sure what is the problem with your set-up.
I can Right Click on any folder, anywhere and of any size and a ‘sendto’ option will show in the drop down with the option to send it to .. Wherever I want.
I have even created different locations in the ‘sendto’ option.
All this on Vista 64 and windows seven 64Bits.