My $0.02 is that this would be easier with two command buttons, but I understand wanting to consolidate them. Actually, it could probably still be done with just one command button. Worth a try...
I can get the disabling of the button to work easily as I have proved this using another control on the form with a control source from the form query, its only when I use the calculated field as the control that neither the test text field nor the button disable work