It was set up as user 1 was my first and last name, gmail address, phone etc.
User 2 was my first name and my company name, so Mark Smith and Mark Apple basically.
User 2 had no other info, name or email etc. - I ended up dragging user 2 to my icloud contacts, it didn't seem to show there, and it appears to be working now. I can't say for sure if thats what fixed it, I messed around with it a bunch of login / logout and seeing it change AFTER the login.
For now, both images stay as expected and I really don't know what ultimately made it stay but I think it was something to do with dragging the contact card into icloud but it could've been something else
I DO KNOW it had to do with the contact card and I GREATLY appreciate that. In this case I thought I could change the Apple -> System -> User -> Edit -- Change the image an be done but there was always an image update at login it seems but all works well now!
If what I said I did with the contact card may have any bad effects let me know!
One final thought - I've had trouble with creating a gmail account with periods in it that gmail ignores but other providers consider a period an actual computing character
ex: "Matt.Jones" not equal to "Matt Jones" - ruthlessly annoying and I wound't be surprised if it created a problem if this isn't normal
