OK I started from the top, create the self-signed cert and server keys with my common name on a test domain pointed to my LAN ip, test in the browser & the video plays on the https common name link, still with the same warning "The identity of this website has not been verified".
I followed everything exactly through step 3f and left the "VerifyClient require" & "VerifyDepth" commented out of my conf file.
When I try to access the video hosted on the common name link with the simplevideoplayer app I got the same result from roku:
"play failed: An unexpected problem (but not server timeout or HTTP error) has been detected."
EDIT: I forgot to update my package 'video.SetCertificatesFile()' with the new keys from this new time around - i did that and it worked this time!
So (theoretically at least) it was failing the first time because of common name mismatch; and the 2nd time I just needed to update the keys - now I need to see if I get the actual security part to work...
Thanks very much for your patience helping me with this Kevin!
aspiring