Ok, that looks like a fairly standard setup. I guess taking a look at the boot loader itself would be the next step. When you see the Debian bootloader you could try pressing ‘e’ to view what commands it uses internally to boot. The lines starting with “linux” and “initrd” would be most interesting.
Hi, it would be useful to know what kind of device you are installing on. For a laptop the model and make would be especially useful. If it is a PC then the drive configuration would be interesting (what kind of drive, how many etc.)
If they are all installed in the same wine prefix you could back up everything in one go by archiving the “.wine” folder in your home. that will include all applications installed in wine and all settings for those applications.
if you want to separate them into one archive per app you should look into wine prefixes, otherwise you would need to identify every folder a given app created during installation and archive those together manually, which can be very tedious.
So it still uses a MSDOS partition table, interesting. This usually only happens on systems that do not support EFI at all.
Is your BIOS and main board fairly old per chance?