Excellent writeup.
I have a few suggestions:
1. Very few programs *really* need to be reinstalled after reflashing. Most programs just make a symbolic link from /usr/local/ to /mnt/cf/_local. If you recreate the link after reflashing, you should be able to run the program without issue.
2. If you're going to be working a lot in the command line, install dropbear on your iLiad. You can then use Putty on Windows, or SSH on Linux to connect to your iLiad's IP address. This makes editing files significantly easier.
3. You can't exactly make a ghost image of the iLiad. If you really wanted to, it's possible to make a modified reflash image. You'll have to acquire the latest firmware image, mount it on a linux computer, modify the file system, and reflash it to the iLiad. It's a lot of work even for someone experienced with it, but if you're going to be reflashing often, it might be worth it. Acquiring the image is the hardest part, but if you can sniff traffic, or ssh to the iLiad while upgrading the OS, it's possible.
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