Originally Posted by nbob
1. System does not automatically boot to the desktop. (I'm stuck back at the command line where I must login and then startx manually).
Were you on Debian 7 (Wheezy) originally and then upgrade the OS to Debian 8 (Jessie)? Or did you make a fresh install of Debian 8?
If you have to login via a command line then it's possible there's a problem with the desktop environment you're using. Are you running Cinnamon?
I think Xfce desktop is default for Debian 8, so are you able to change the desktop environment to Xfce. If this remedies the problem then at least we know it's a problem with the GUI.
2. Network-manager icon keeps disappearing from the notification bar. I have tried manually re-installing network manager but the icon just won't show up for me in the notification area. I'm not even sure if anything is broken here but it is irritating.
This may indicate a problem with the desktop environment not having the right drivers for your GPU.
I'm using Debian 8 with Cinnamon desktop and have found that some functions are buggy because Cinnamon doesn't have the drivers for my old radeon integrated GPU.
Do you have an AMD CPU and what GPU are you using?
Incidentally, which linux kernel do you have? (uname -a)