OK, I decided to test Raspbian's upgrade abilities using both one of my old Raspberry Pi 1 Model B's (I went for my 256MB model), and my new Raspberry Pi 2 Model B.
I used an 8GB micro-SD card (SanDisk Ultra Class 10), with SD adapter for my original Pi, and a USB SD card reader for my PC.
On my Windows 7 PC, I downloaded the earliest official Raspbian image, 2012-07-15-wheezy-raspbian.zip
, extracted it, and flashed it to the micro-SD card using Win32DiskImager.
It booted up on my original Raspberry Pi 1 Model B (256MB) - quite retro now to use an image from 2012! I configured it with sensible options and rebooted, where it automatically expanded the file system to the full 8GB, and finally booted to a command line.
I ran the update commands, as before:
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sudo apt-get update
sudo apt-get -y upgrade
sudo apt-get -y dist-upgrade
sudo apt-get -y install raspberrypi-ui-mods epiphany-browser pistore sonic-pi minecraft-pi wolfram-engine
This of course took a LONG time for such an old image on an original Raspberry Pi. (I noticed that it is indeed mandatory to run apt-get upgrade before apt-get dist-upgrade, or the update process fails.)
Where it prompted during the update, I selected the default options (possibly not the best choice). I also accepted the Wolfram licence agreement to install Wolfram Mathematica.
On launching startx after rebooting on the Raspberry Pi 1 Model B, the improved UI was operational. I removed the desktop icons (other than Wastebasket) as in recent Raspbian builds. I then shut down the Pi 1, and tried the micro-SD card in my Raspberry Pi 2.
Success, it worked! I couldn't get sound working even after adjusting all the HDMI config.txt options (probably something trivial to fix), but other than that, I can confirm that the very first official Raspbian image from 2012-07-15 can be updated on a Pi 1 to work on a Pi 2. (The card also booted fine when I put it back in my Pi 1 - I tried it successfully on both my 256MB and 512MB models.)