Messages cannot be processed until your application re-enters a message loop, so any attempt to modify/update control state that relies on message processing will not work within a single sequence of code that does not "pump" messages.
Fortunately the VCL controls typically provide a means for force repainting without waiting for messages to be processed, via the Update method:
Button1.Enabled := False;
Button2.Enabled := False;
Button1.Update;
Button2.Update;
This works independently of having to disable form repainting. The form will not repaint until your application goes into a message loop anyway, so disabling form painting and re-enabling within a single procedure that does not itself cause message processing is a waste of time.
This may not be exactly simultaneous repainting of the two buttons, but truly simultaneous painting of two separate control is impossible without getting into multithreaded GUI painting code which I think is way beyond the scope of this problem. Calling Update on two buttons in this way will be as near simultaneous in effect as you need however.