Your mileage may vary, but Chrome Remote Desktop might be the easiest solution for remoting into the chromebook: https://remotedesktop.google.com/

My grandparents (both in their 80’s) have some iPads, phones, and a Windows laptop as well. It has been interesting learning about how they use them and what specific issues they encounter and how they deal with them.

The Windows laptop was the first thing they abandoned. They like to pick up their devices, do a quick search online, then close them up and put them away again. They may not use the device again for another week or more; longer for the laptop. This meant that they used the laptop so infrequently that whenever they did try to use it - the battery was always dead and they would get absolutely hammered with Windows updates. They would then unplug the machine which would cause it to die (dead battery) when they were done using it for a few minutes, killing it mid-update. Multiply this a few dozen times over a year and you have a very very unhappy laptop and frustrated grandparents.

The cellphones were another major issue. They’ve had several iPhones and a couple dumbphones/featurephones. The issue with the iPhones were the complexity and screen size. Trying to get an 80+ year old senior to use a tiny touchscreen keyboard is simply out of the question. Only one of them could read the screen and that’s because she had Lasik eye surgery. They also kept running into annoying little problems that I would have to fix whenever I visited. For example, they could not grasp the concept of a long-tap and how it invoked additional options. No matter how many times I instructed them, they simply would not lift their fingers off the screen fast enough. I highly recommend adjusting long-tap delay timing if you have elderly family with the same issue but this will vary greatly by device; I don’t think the iPhone had it. The dumbphone worked a bit better, especially as we got them one with big chunky buttons they could easily see and press. The problem was that they used it so infrequently that the battery was always dead and they always lost the charging cable and/or forgot which cable was which. To this day, they basically never use it and we’ve been trying to get them to cancel the phone plan for it because it’s wasting them money.

By far the biggest success has been their iPads. They really enjoy sitting in their chairs and browsing the net with the larger, brigther, and clearer screens. I adjusted font sizes to be easier on their eyes and they both find it much easier to navigate on them and press buttons. The long-tap issue is still here but it’s not as bad. They’re less likely to inadvertently tap stuff because they can see easier. I still have to put some stuff back into place when I visit them, but that’s just normal grandparent-visiting stuff.

side note: One thing I noticed they really hated across all devices (and frankly, I hate it too) are pop-ups. Not pop-up ads because I blocked those for them, but app or system pop-ups. If they open an app and they get hit with 15 unskippable tutorial pop-ups, they will just hit the lock button and walk away. They will come back later, wake the device up, see they still have to go through with the tutorial, and then call me and ask how it “broke”. I highly suggest configuring devices to minimize this as much as possible. It makes them feel like they are losing control over the device and makes them panic or get frustrated, and honestly I can’t blame them. It’s horrible ux design.

For reading news, I recommend getting a tablet and a case with a stand to prop it up at a comfortable reading angle. It’s easier to read with aging eyes than a smartphone. It will still have the accidental long press problem, but icons need to be dragged a longer distance to be rearranged so there is a better chance it will snap back into the right spot after an accidental long press. Someone needs to make an elderly-proof launcher that has a way to lock things in place on the home screen and disable that long press there. Maybe someone already has? I haven’t played with alternative launchers in years.

I use Blokada 5 on my android phone which is a free, phone-wide ad blocker that runs as a local VPN based DNS service that blocks spam address DNS requests. They do have a newer version, 6, that’s cloud based instead of a local VPN and requires a subscription and I haven’t tried that out. Maybe that one is easier to reconfigure remotely if something important inadvertently gets blocked. The only reason I never tried it is I have a very limited income right now as a full-time caregiver. I have used Blokada 4 and then 5 for several years now.

My pi-hole on my home network is also pretty set it and forget it and protects all of my mother-in-law’s devices while she is connected to the Wi-Fi, which is most of the time since she only ever wants to leave the house for doctor’s appointments or occasionally to eat out. I bought a cheap orange pi zero to set the pi-hole up on and it lives next to the router. My MIL is a 70+ year old gamer so she is a little bit more tech savvy than your average elderly person, but she constantly falls for ads and terrible tabloid clickbait that shows up in her news app.

I kind of want to try setting up an RSS app for her with more curated news sources and see if that will give her a satisfactory news feed without all the junk. I used to use Google News, but it has become nothing but spammy tabloid links with no relevance to me. I mostly got my news through Reddit in recent years, but Lemmy reintroduced me to RSS and I’ve been working on collecting good news sources like back in the good old days before the social media firehose of info.

Unfortunately (for the purpose of offering advice), I have no experience with remote tech support. My dad is a retired computer engineer so he’s got a handle on things at his place. I live with the tech-challenged person in my family.

My mother (mid 70s) and grandmother (early 90s) are obstinate. They wont even TRY to learn how ANY tech works. Neither even understand how to use their dumb cordless house phones 99% of the time. They both have dumb flip phones for emergencies and neither has a computer or tablet.

2 things I can tell you. 1. Regardless of what they WANT, get them tech that YOU can work with, and refuse to help them with anything else. And 2. Set realistic expectations, from the get go, on how much you can/will help them, and what YOUR schedule allows. Maybe it’s because my family are all narcissistic assholes, but they will suck you dry with the constant needs. I find that the older people get, regardless of their personalities they seemingly all get way more needy like toddlers or worse.

I strongly suggest getting them to check out their local library. Library staff often have knowledge and practice working with older people who may have skills deficits. Even if there aren’t formal classes, often, someone will be willing to help. Sometimes, branches have a dedicated tech staffer. That can spread the workload out a bit, and allow them to have someone local to help, as well.

I don’t have any great advice for phones, so definitely looking forward to reading everyone else’s replies, but:

I gave up on trying to figure out how to remote into the chromebook.

Does Chrome Remote Desktop work on Chromebooks? I’ve had really good luck with this in general for PC support.