>Why do I have to do this 'DTOC(CLEARED) + DTOC(SETTDATE)' when I really want to do this '(CLEARED) + TTOD(SETTDATE).' Am i missing something here?

Are you creating an Index expression? What exactly are you trying to accomplish? Your second choice creates an error because you are trying to add 2 dates together. You can only add or substract a number from a date.