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I'm no tech genius, but if I were doing this, which is very generous by the way, I'd type up a very simple 'cheat sheet' outlining login instructions, navigation to specific site / app instructions and sign out instructions, laminate it and then adhere it to each of the Chromebooks palm rest area. Making sure to use a nice clean and large font obviously.
Then for configuration, I'd set up each Chromebook with the apps you think they will use and allow access to these apps for all users.
I'm not sure how many people are at these homes, but I'd carve out an hour when you take the computers down there and show the staff how to create an account. Have staff keep password backups incase they forget there logins, so they can assist.
The problem with all of them using a single account for instance, is there will be too much HTTP stored and will make contacts and app navigation more complicated.
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