Thanks everyone.
I went with Cory's dual box option. The main macro now calls out a sub-macro that contains a dialog box and the IF MESSAGE box. The dialog box with the check list items inside opens first. Then the IF MESSAGE box opens so both boxes are open at the same time. The dialog box in the sub-macro is set to close when the sub-macro ends, so both boxes close at the same time. All nice and easy.
Paul, the add on program is nice, but there were too many IT red flags. I would not be allowed to use it. It says in the instructions, "It's a very ugly system hack that sits in your system tray...This small hack is completely and utterly free and we accept no responsibility if it causes something to misbehave! It -=IS=- a HACK! "