Hi. Im running Debian 8 on my pc. Did nothing too drastic to the system other than update/upgrade and I ran bleachbit once. I don't know how but somehow something got deleted that I need. I really have 2 issues:

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).
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.

Any help would be appreciated!

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.

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)

I don't know about changing the desktop environment. I installed xfce and haven't attempted to change it. When I enter 'startx' from the command line it brings up my xfce environment. Is there any chance the operating system is confused which desktop environment I am using? And if so, how do I double check that setting.

uname -a: Linux debian 3.16.0-4-amd64 #1 SMP Debian 3.16.7-ckt20-1+deb8u4 (2016-02-29) x86_64 GNU/Linux

Yes, it was a fresh install of Debian 8.
I'm using AMD with a NVidia GT-430 video card.

I use bleachbit to clear out my junk. Would this cause this behavior somehow? It seemed to happen right after I did my housecleaning with bleachbit.

Try visiting the Debian site and installing drivers for your NVidia video card:https://wiki.debian.org/NvidiaGraphicsDrivers

There is an interesting bit on the debian web page which says 'The proprietary drivers don't provide normal logging and can be a hidden source of problems.'
You should follow the instructions on the web page at the beginning in case they sort out your problems more quickly.

I reinstalled everything and went with the opensource video driver nouveau. I think my problem was that I was trying to get the proprietary nvidia driver up and running. I was trying to use the sgfxi script to do this. Apparently, there are some issues with that method.
So far, so good!