The most important factors to consider are the following:
- 2x256 MB is usually cheaper than 1x512 MB
- Some current DDR motherboards don't like running with 3 sticks of RAM (they revert to lower speeds, nForce comes to mind)
- 512 MB may be slightly less overclockable because they are higher density than the 256 MB sticks
- 512 MB sticks almost always come out after the 256 MB sticks
That being said, I'd go with the 1x512 MB for expandability purposes.  I have 1x512 MB Crucial PC2100 running at 150 MHz FSB (300 MHz effective), and haven't ahd any problems.
-Ice
PS your friend is on crack, as stated above the system sees memory as a continuous list of addresses.  What's stored in RAM is at a much lower level than a file, your friends comment is blatantly ignorant.