I've known him nearly two decades. He struggles to follow the simplest of instructions. He can screw up just about anything he's left alone with. e.g., to clean, he disconnected the composite cable between DVD player and TV, then couldn't figure out why it made a buzz when he tried to play a DVD after hooking the cable back up to the wrong input and output connectors on player and TV. (Vizio helped confuse, by providing no yellow input, and microscopic instruction to use the green instead.)

He needs to be able to get online to pay bills. He's too poor to have anything better than Juno, no broadband or wifi, so POTS it has to be.

I just deleted the Vista partitions from his Sony laptop, which has 4GB RAM, 1280x800 965GM video, Core2Duo. New partitions are ready to install to.

Which DE would you suggest for this kind of person's laptop? Which DE might give him, and me in dealing with him, less frustration than the rest?

I find Cinnamon to be most friendly, but I don't have a lot of experience.
I gave up on KDE mostly because it kept crashing...that probably could have been fixed...but I found I related better to Cinnamon, so just didn't try to fix KDE.

Are you really sure you want to give them anything, if their as "dimwitted" as you claim? As I fear there might not be anything you could give them, that their not going to "screw up" if their as "dimwitted" as you claim. In that case, I'm not even sure it's wise to give them Linux full stop. I don't really have a specific DE for you to let them loose on, but perhaps maybe you should just convince them to use Windows instead in that case?

FWIW, if I was going to recommend anything, it would probably be KDE or similar.

While I haven't used Cinnamon myself, and it was many years ago when I last used GNOME, I found a very similar thing with GNOME - ie. there was always a problem of some description with it. That's why I gave up on it and moved to KDE instead. While the first versions of KDE 4.x were completely unstable, other than that, it's always been quite good to me. I haven't really looked back since (other than the first versions of KDE 4.x, but KDE 5 when I last used it was much better). Although, I'm not a fan of the look of Qt 5, I must admit - Qt 4 looks better IMHO.

In such cases I would go for a minimal Xfce setup with a single panel. I would steer away from KDE as, from experience, people will start dragging stuff around and making a mess. You could of course have a simple shellscript which restores configurations from a backup at login.

You could also consider a simple window manager with a minimal panel with just the button to launch their favoured browser and keep it all as no frills as possible.

I have limited experience and it's years since I've touched it, but gnome is also developed from the perspective removing the user's options and customisations to ensure that gnome is recognisable as a "product". It may also be a good option due to these restrictions.

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I'd suggest you do a remaster of a distro such as AntiX or MX, (very easy to do on these two distros), give him what he needs only, then make your remaster of it, & then install it to his computer as a frugal install, that way, if he messes up his working session, he should just be able to shutdown & reboot, & be back to a good session again.

https://mxlinux.org/
https://antixlinux.com/

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@OP how much time do you want to invest? My personal preference is openbox with tint2 taskbar and a background setter, use obmenu to edit the right-click menu and that's it.

He logs in and right-clicks the desktop to select his apps and that's only the apps you decide to add. It's clean a fast.

Based on your colorful description of them:

(1) My own life lessons are maybe that you ought to try to re-orient your thought processes about them. Not very charitable if you think about it. This is your friend or family member, and you've known them this long for a reason. (Sorry: Off my soap box)

(2) I don't think it's too relevant for them, what you give them, so long as it fulfills what they need or wish to do with a computer.

(3) Make a full backup of the exact first thing you gave them. If they reconfigure the system so that it no longer functions, you roll it back to day #1.

(4) Which leaves you with the everyday data:

1. My wife doesn't care to be technical. Meanwhile she has email, bookmarks, online accounts, pictures, E-purchases, ... For me this is all her phone and tablet.
2. Her contacts, pictures, videos, bookmarks, and emails are all on the server and backed up there. Even if she deletes a picture, video, or email from her phone or tablet, (i) it is likely on the alternate tablet vs. phone and (ii) it is online and can be grabbed. As a result of this, she's witnessed that I can get stuff back and also learned that it's not this great idea to delete all her emails and stuff, she's learned to leave them and organize the ones she doesn't care about into a folder.
3. As far as E-purchases; books, music, magazines, subscriptions, this somewhat boils down to (i) the next topic about online accounts, and (ii) retaining and organizing emails. If you buy books or music via Amazon or Google, you have an account which allows you to retain your former purchases. You also typically have emails which give you links to download what you bought, or at least confirm that you bought it, and from where, so you can go back to the seller and ask for a copy.
4. Online accounts, be they bank, medical, Amazon, Google, other email/services, merchants, ... you really have to just work with them to organize this. Because some accounts require periodic password changes, or some accounts you use, but use so rarely that the password has never changed, and you still need to remember it. As potentially damaging as it can be; myself, and my wife from being taught by me, both do write down as much info as we can to aid us with full recall. I.e. say one of my passwords was P*%%word. It is (good or bad) a recognizable word, but modified to fit the rules of most algorithms. Hence a 'hint' I'd use would be P...ord. I'd know it, but you'd have to really know me a lot to derive it. Another thing is that they could create a complex non-word like seaportwheelbarrow, and then perform manipulations to the capitalization and substitutions for numbers and symbols in a consistent manner. For secret questions, I try to use mainly the same ones and I also abbreviate my hints that I have for myself. I also try to maintain the same username for many accounts, or better is that many accounts use your email as the username.

You can do what you can about protecting this person from their inadvertent system instabilities, one of which is the very first thing, adamant backup of the first version. After that, if they're installing software and stuff, then perhaps you ought to periodically visit for an incremental backup. And then you really have to try to just protect what I call, their "state-ful" data. All the phone numbers, pictures, downloads, etc.

Just some suggestions. I realize it can be difficult, I've helped family members who tend to frustrate as well.

And please avoid using S*@portwh**lB@rroH !!!

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Wonder if a live system would be better? You could keep sending him DVD's or usb's and he could be up to date. Dunno, just thinking.

To be fair to this person you should be more compassionate in your phrasing. He may be a great lover or artist or other qualities.

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I'd recommend Xubuntu or Mint Mate. Both Xfce and Mate are easy to use and Clem recommends the Mate version of Mint rather than the Cinnamon for beginners. Set it up and warn him not to tinker!

Forget what DE it has. The important thing is that you make less work for yourself, fixing it when he breaks it. The answer is https://porteus-kiosk.org - It resets itself every time you reboot.

The only other option would be a limited rights guest account, because it's better to log on as a full user once a month to run updates than it is to keep having to fix it.

Self driving car.
Slip on shoes or velcro.
Should not be allowed out in public unaccompanied.

I've set up PC's for him several times over more than a decade. The backup method I've used has been multiple partitions, separate /home, and cloning / onto another partition on the same disk, so that I don't have to keep track of backup media here for a PC I don't own and won't remember details about next time I see it (if ever). This method only works until he gives the PC away, which he's done every time so far except for one time when he gave one back to me.

In the past I had always given him both Windows and Linux, but about the only time Linux was booted was when I was with him. This time he's not getting a Windows option. There is no available license within his budget of $0.

I'm at a loss what this might be supposed to communicate.

Cinnamon is out, as is anything built on a GTK3 foundation. Whatever I pick by default is going to have a start button on the lower left corner and a clock on the lower right, just like WinXP, and KDE at least since V1..1.2 (Mandrake 7.0). That rules out XFCE, and IIRC, Mate also. His Vaio resembles a Macbook, so I had entertained the MacOS imitation, Elementary, but it seems to be unavailable without spending money.

Using a live stick seems to me is unlikely to be able to negotiate the Juno/POTS hurdle. Free 10 hours per month is all his budget covers.

My current leaning is to Q4OS, but Mill J's suggestion is intriguing. Limiting him to email, calendar and his bank is probably close to what we both need.

Mate desktop allows you to customize a LOT. The Mint Mate desktop looks almost exactly like their Cinnamon edition. In other OSes, it takes a LITTLE customization, to move it to the bottom and tinker to make it look windows(ish).

How about keeping a backup of the system In its initial state. Then set him up with Firefox bookmark sync and file backup (mega.nz - 50GB free and good linux apps). That way, it can be restored to 'factory settings' in about 15 minutes, and his files and bookmarks back in another 10 minutes max.

Another thing: limit his account, so that he can't run anything with elevated priveleges. No software install etc. Of course, this does mean that he would not be able to update it, but he sounds like the sort of person who might switch it off while it is updating anyway.

I apologize for confusing you with a joke.

Earlier in my post I had been talking about using regular words, modified to be passwords, and mentioned making up a combined word. I gave the example "seaportwheelbarrow" and then altering parts of the word, such as use @ for 'a' and use 8 or * for e and other types of letter substitutions.

That joke at the end was a modification of that example seaportwheelbarrow changed to S*@portwh**lB@rroH implying something attune to, "Hey, don't use what I've already refined to be my password!" Which it really isn't. Sorry again, just bad taste.

I realize they are a difficult person to aid. I feel the suggestions of either live distros or limited access distros would be helpful.

The DE aside, I would suggest that the OP install TeamViewer or equivalent (with emphasis on ease-of-use) on their friend's computer, and give them instructions on how to use it.

I support several less-techy friends, and very often the best approach to a problem is "Give me a few minutes and I'll TeamViewer in and sort it out for you". I go in, resolve the issue, and get out again. Job done.

This DE search seems all for naught. I tried by starting with basics, determining whether the modem could work at all. My support mailing list discuss-subscribe@linmodems.org sub attempt was returned to sender. ScanModem found a 14f1:2c06 High Definition Audio device that should be supported as a modem, but underlying support for modems in distros seems to have died through lack maintenance required for newer foundational software versions, e.g. glibc, gcc, etc. The driver has to be built, and automatic building by installing the .deb (Debian 10) or .rpm (openSUSE 15.1) fails with "C compiler cannot create executables" on the cli and in config.log. In Debian, every attempt to use apt or aptitude for anything since trying to install the .deb results in "E: Sub-process /usr/bin/dpkg returned an error code (1)" on account of alsa-driver-linuxant producing exit status 77 in post processing.