I've often seen normal people come up with deeply nested directory structures with long descriptive names and they get bitten hard by the 260 character limit. For example names like this are very common in my experience:

    C:\Documents and Settings\Joe Random User\My Documents\Some Cloud Software\Company\Projects\2013\156 Big Customer Inc\Locations\Someville Foostreet\Problem reports\2013-10-07 product not working\images\video of product not doing what it's supposed to do.avi

Also:

    find . | python -c 'import sys; print max(sys.stdin.readlines(), key=len)'