The Year() function returns and integer which you are comparing to a date.
IF [Date Signed] > #2016/06/30# THEN [Grand Total $]
ELSEIF [Date Signed] < #2016/07/01# THEN [Grand Total $]
Ivan - thanks for this. I see what you mean. Taking out the YEAR part makes the formula valid. But it doesn't seem to limit the bookings to just what occurred inside the date range. My intention is to limit the bookings to what should be inside this date range.
Well it looks like i've answered my own question here. Putting in an AND operator seems to do the trick. I am now able to put the two measures on a bullet chart quite easily. Good to go.
IF [Date Signed] > #2015/06/30#
AND [Date Signed] < #2016/06/30# THEN [Grand Total $]