You can do Dist-Upgrades not only with the GUI update-manager but also via do-release-update. The tool tells me what awaits me (I have 6000 kB/s):
66 packages are going to be removed. 193 new packages are going to be installed. 1269 packages are going to be upgraded. You have to download a total of 1005M. This download will take about 23 minutes with your connection. Fetching and installing the upgrade can take several hours. Once the download has finished, the process cannot be cancelled.
So, let’s see.
Btw do-release-update by itself notices if you are connected via ssh and asks if you want to proceed. If you do you’ll get a second sshd on Port 9904. Using screen it shouldn’t be a problem for me but very nice of the tool to ask :)