I performed similar task (dist upgrade to squeeze) and ended up with the chain loader (what I wanted).
the chain loader to grub 2 worked just fine, I was happy with the operation of grub2, everything appeared to work correctly (all boot options checked out), so followed the option to remove grub-legacy.... upgrade-from-grub-legacy after which system failed to boot, no menu options where prescented.... Problem resolved by booting from a live CD, chroot to my linux partition then grub-instal /dev/sda Sorry can't remember exact grub error message... --------8<------- Additional: having run grub 2 for about a week now the bootloader failed again. this time Grub 2 would start but would inform me that it couldn't find any installed modules, continuing would prescent the usual BIOS can't find system disk error Adian ruuning grub-instal /dev/sda appears to have recovered the system, and I once again have my boot options for a few kernels, 'doze and 'doze re-install on the lappy. Regards Andy