Debian 8 to Debian 12 upgrade - involves BRLTTY (yikes)

[hotmess]

I have been asked by a friend to help his unsighted friend update Debian 8 all the way up to Debian 12. Before that, I'm supposed to clone the old drive to a newer drive. (That part I think I've got a plan for.)

But such a big jump - 8 to 12 - and I'm a new Debian user myself. Am used to Linux, and all other things considered would just do a standard update. Except I'm worried about a few things.

1. Is anyone running BRLTTY - an app for sight-impaired folk who know braille - on Debian 12 here? Does it work pretty well, or are there issues? And will config files from a Debian 8 install still function correctly in Debian 12?
2. Can Debian 8 be upgraded all at once to 12, or (as at least one person suggested to me) incrementally? 8>9, 9>10, and so on?
3. Are there other pitfalls to watch for or, on the other hand, things to expedite an upgrade? This will be of course a NON-graphical environment he's got, so I don't want any update suddenly choosing to give me a graphical desktop. He doesn't need or want it.

I will have my own Debian laptop with me (a MacBook Pro 2011 13") with 12 already on it. Worse comes to worse, I can pull his hard drive and get into it with my machine. I'm really hoping that will not be necessary.

That's all I know to ask... but would greatly appreciate guidance. I'm due to try this all on this coming Friday (Oct 20).

-jon

[CwF]

I start with the worse case assumed, I like pleasant surprises, not stalls...

I would always recommend a new storage device for something spanning this time frame, even with every confidence the old device is fine. Don't back up, upgrade up.

I would use qemu-img from package qemu-utils. I would usually image the original to a file, image the file to the new device, install the new device, confirm operation, proceed with the upgrade. Image the original before any changes, and ideally don't apply any changes at all to the original.
About that image file stage, I would usually upgrade that image in a libvirt (qemu-kvm) vm, then image the result to new the device.

Yes, upgrade through every release incrementally, test each result before proceeding.

Who's doing the upgrade? I would strongly recommend establishing a secondary user configured however you like, and use it to administer the upgrades. Bounce into friend user for each check step. You should have multiple paths, establishing ssh function from your laptop wouldn't be a bad idea also.

This may be the long way, the expensive way, and also the no fail way.

As far as the BRLTTY factor, sounds cool, and I don't know.

[dilberts_left_nut]

There is a LOT of changes between 8 & 12, and yes, you will need to go through every upgrade between.
I would very seriously consider a fresh install, restore old data, and configure to suit.
It will be an order of magnitude quicker and much less likely to cause disruption.
At any time up until the new system is "ready" the user can simply plug the old drive in and continue with the old system in the mean time.

[artytux]

I would lean towards @dilberts_left_nut post on doing a fresh install, would be quicker and cleaner on the system, one other thing is that until you get the machine upto date on Debian 12 you'd be in nowhere land not Linuxland if something should go plopity blah blah plop could even happen from upgrading Debian 12 just after you've finished.
If it was me I would consider that too big a risk/hassle of not only failing the upgrade process at any step(S) also the the time spent doing all this work,
Unless it really miserable outside with rain and wind nah not even then.
I second the fresh install Vs risks of a failed upgrade from 8 to 9, then 9 to 10 then 10 to 11, then 11 to 12 and wow no I would not do step by step.
Unless of coarse outside it's rainy and windy I'd make a bread and butter pudding.

The reason I'm posting is not so much for the above but lately I've had a big curiousity about having separate / and /home, , I 'd like to know if you intend on having separate / and /home or you already have that on board?.

Best of Luck this weekend whatever you decide
Let's hope it's all good.

[hotmess]

Thanks so much for your thoughts, @CwF @dilberts_left_nut and @artytux - you answer questions that raise new questions. And mostly I realize how little I know about large areas of Linux, despite having used it (along side other OS) for a long time.

First, I am quite constrained here, because I don't want to (frankly) create a situation in which I become a continual geek squad for the guy who owns this older machine (an HP 6000 Microtower with - I think - 2g memory and a spinner, it now turns out, hd). I live just far enough away to make that problematic. I don't think he has a separate /home directory (which like @artytux am a big fan of creating on my own machines). If I were funding this beyond the time I am putting into it, I'd buy a better machine and two ssd drives - 500g each would be more than enough since the system he uses is so light w/o all the graphical apps and desktops.

Second, he's constrained. His OS is non-graphical through and through, for obvious reasons... no need for graphics in his case (plus, 2g?!).

Third, how does one do a non-graphical fresh install of Debian? I just... have never installed any OS (since MS-Dos - yes, I'm older) non-graphically.

Fourth, there is hardware that goes with the BRLTTY software. And that's the scary part. Will everything just handshake the way it did previously?

I will be googling all this, too. Just figure asking the questions here is closer to where good information is than google. Thanks again for your help so far and to come.

[CwF]

Fourth, there is hardware that goes with the BRLTTY software. And that's the scary part.

https://packages.debian.org/search?suit ... rds=BRLTTY
It appears you're good to go on a fresh install, I'd expect success.

I'd buy a better machine and two ssd drives - 500g each would be more than enough

Wrong thinking in my ways. A 120-128 ssd is very cheap, and will hold any OS. As you mention, relocating /home helps, but instead I leave /home on disc and mount excess storage under the user's standard directories. This makes the OS small, including "dot" files in /home. Backing up, upgrading up, making images, etc is much easier when the OS is only what it needs to be. Even 100GB of empty disc slows down the process, let alone all the extras people have on their one giant disc poised for disaster.

Second, he's constrained. His OS is non-graphical through and through, for obvious reasons... no need for graphics in his case (plus, 2g?!).

I still suggest establishing a second user, with full rights. A stripped XFCE will offer everything from a right click on an empty desktop within 400MB memory and a disk footprint of <100MB.

Third, how does one do a non-graphical fresh install of Debian?

Precisely why I recommend a second user, minimizes considering things that don't need to be considered. I'd assume the original home to coexist fine. Pay attention to guid if on a fresh install, create the original user first. Also consider how the login is handled. If there is no logon manger then I would set up this secondary visual desktop for visual IT use to be autologin on tty2+, so the original is unchanged and Ctrl+Alt+F2 goes to 'your' desktop.

For many people this can be important. I'd focus on your image capability and get that right, then you're covered from disaster.

[artytux]

CwF seems to have covered the a couple of extras I was going to post, cool.
A considered to be small is plenty big enough as CwF wrote.

Did you know that Backintime and Timeshift can be both run on a schedule, on another (small/cheep) ExtHD.
as I do so no need for human intervention ?
Want to know my schedule, wont bore you with that, unless want/need details.
In the unlikely event then you have peace of mind and can return the machine and OS *back to* when all was well.

Just figure asking the questions here is closer to where good information is than google

:100%

Good Luck this weekend.