I have not personally experienced any shapefiles with a leading underline. You are probably right on that one.
Yes, I agree.
As to whether MapSuite should enforce this... I'm not sure. Where do you draw the line? We have in-memory feature layers that don't have any column naming issues... people us long names, etc. And "missing values" can truly be null. When we want to "export" these feature sources to shapefiles, should we expect that the MapSuite tools will somehow make good filenames for us? What would be the rule for handling column names that are too long? What would be the rule for handling null values? Historically, we have always just accept responsibility for these things in our own export wrappers. Not sure if that is the right approach, or not.
Should the export routine throw exceptions on known issues, and let you fix them, like the layer redraw exceptions?
Maybe we should convince the world to move to something better than a shapefile :)