Just to answer some questions before we dig in:
Why am I using the LXDE? I like it better than gnome and xrdp works. xrdp is the single biggest thing for me.
Why do you need virtualbox? I need anything that can run the common, vmx and iso type of vms. I dont care what software I use for this, if you have something that works better, please let me know.

I'm not trying to do anything crazy or fancy, just update the operating system. I've been having this problem for a while now, so I saved exactly which commands I've used since I've installed. Hopefully someone smarter than me can recreate this and figure out why exactly it's breaking.

Code:
apt-get update -y && apt-get upgrade -y
yes services can be restarted, no don't change the mac
apt-get install xrdp
service xrdp start
service xrdp-sesman start
update-rc.d xrdp enable
apt-get install virtualbox
apt-get install geany
apt-get update -y && apt-get upgrade -y
Now when I do that last update/upgrade I get this

http://pastebin.com/ydYqvBmU

Thanks for your help.