Fri Oct 04, 2019 7:32 pm
You can likely continue down the rabbit hole of resolving dependencies, once you bottom them out you will be able to install everything and it should mostly work. You may still have issues, and certainly will have unused, unwanted leftovers from the last version of Debian. The more exactly stock your install of Stretch is, the more likely it is that an upgrade will work.
Given that SD cards are so cheap, and it is so easy to just use another one, the better approach as fruitoftheloom pointed out is to start fresh with Buster. Load it on a new/different SD card, using Etcher. Once you have it up and running, add in your extra apps and then just mount your old SD card via a USB adaptor and copy across any data you want to keep. This will likely be faster, will certainly be easier, and will ensure that you have a functional bootable system (with your old Stretch image) and all your data will be safe. Once you have everything updated to Buster and fully working you can recycle the old SD card as whatever (a spare, a backup copy of your current card, reserved for the next OS upgrade, etc)