Wow, a lot of great info.
Did you by anychance use the "symbolic" menu entry for Debian based OS's that I posted? I am just curious about that. They are all I use as it keeps my menu short and sweet.
You can have 2 entries per OS if you want. Just edit the instruction string to read "..... ro single" dropping every thing else. I never do it is shorter without it, editing the entry to read that way for one boot is fast (how often do you need recovery mode?).
I think that may cure the file system problem. Really sounds like a script problem to me, makes me wonder about the integrety of your grub install.
There is a slight chance, but a chance none the less, of malware infecting your MBR. Testdisk will right new, blank, code to the MBR if you think that at all a possibility. You will, of coarse, have to reinstall grub to your MBR after that.
Ubuntu started using Grub2 first (as default boot loader) of any distro. I was testing the dev release version of 9.10 when that was introduced one day right after alpha 2. No documentation. What a ride. We, the testers, spent 2 weeks editing the grub.cfg file directly to tweak things. Slowly learned how to deal with it.
That first iteration we got would not boot the OS it was on if the OS was installed on 2 partitions. A single partition install would boot other installs that were installed on 2 partitions. Just plain weird.
The Ubuntu community documentation is the best for Debian based installs using grub-pc. RH branch installs do not even use the same commands to install or update grub.
https://help.ubuntu.com/community/Grub2
The best thread to get on to for answers to the stickiest problems is on the UFs, if you can stand that outfit.
http://ubuntuforums.org/showthread.php?t=1195275
The OP there was one of the testers in 9.10-testing. Did a lot of research and shared it. Did and continues to do a lot of experimentation with grub-pc. Pulled all of the discoveries that all of us made and started the basis for that linked thread on the testing forum.
He is also the main perpetrator of the Ubuntu Community link I posted.
While I have given up on Ubuntu and particularly their Officail Forums, there are people and threads I miss there. Drs305 and his many threads on how to make grub-pc sit up and beg being at, or at least near, the top of the list.