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You may want to reconsider an iPad (or anything touch-interface). Tried it with some older relatives, and the UI differences ended up being too much. Additional

You may want to reconsider an iPad (or anything touch-interface). Tried it with some older relatives, and the UI differences ended up being too much. Additionally, even though my grandfather is a hunt-and-peck typist, an on-screen keyboard was far more frustrating for him to use. At least have him try a tablet first. Consider that touchscreen keyboards in general are harder to use for people with poor dexterity, especially for new users. Chrome book with an adblocker should be reasonably secure, if you're worried about scammers there are other possible attack vectors that having a secure computer won't defend against. Consider that if he could fall victim to a windows virus scam, he can just as easily fall prey to the myriad scam telephone calls. Unfortunately, there is no easy tech solution for this; either educating them or setting up financial safeguards through the bank will solve that problem.

mlac 7y ago
Fair point... And I get that education is key, but I'm trying to throw up technical solutions as best I can so they can maintain their online freedom. I'm thinking routing their DNS to a pihole, getting them a static IP so I can VPN in and access their Mac, routing their Chromebook to the home network with VPN so it goes through the pihole as well, and then locking down permissions even further on their accounts. If I have solid remote access through VPN I'm comfortable having him call me when there is a need to install something... Their use case for the computer hasn't changed much so I don't anticipate they would need to make a significant number of installs. And in terms of banking maybe we can make a few calls to their institution.