I want to say sorry to the Microsoft folks fro calling Windows Live Mail buggy. Still I am not sure why there were two places not checked off on my brother's ID but the others were. Those two little missing marks caused all this brouhaha.
The solution was left side button to get to Options - Safety Options - Security - Digital ID's - other people - highlight the ID you want then hit Advance. You will see many check marked items called Certificate Purposes. All things there should be check marked. If not, then mark it.
That was my problem. For some unknown reason two of those were unchecked.
I do hope this information can help other people who have a similar problem like I did,
REN88