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New So, it works.
Fresh install of Ubuntu 10.04LTS upgraded to 20.04, and the only third party tool I had to use was a gparted boot ISO, because I stupidly made the initial vmdk image far too small. 32GB should be your minimum; at 10GB you're going to hit capacity issues.

As per my advice to drook on Slack:

Ensure you have quite a lot of time set aside. This will take at least a couple of hours; quite a lot more if your storage is rotating rust and/or your network is embarrassingly slow
Ensure that you have at least 10GB spare disk space and/or do "apt-get clean" between versions; the upgrade is not stupid and checks first
I had to comment out the third-party repository in sources.list
If this machine is virtualised, consider removing the VirtualBox additions (other virtualisation solutions with similar auxiliary packages are available) - could have been coincidence, but I had a hard lockup at the GDM screen when upgrading 10.10 -> 11.04.
The order of releases it chooses is a bit weird at first - Mine went 10.04LTS, 10.10, 11.04, 11.10, 12.04LTS, 14.04.LTS (and so on) - just roll with it
Remember to pass the flags for saying "yes" to everything if you want this to be even slightly unattended-flavour

Also note you can give do-release-upgrade, which is very conservative by default, a kick by adding the "-d" option.

Original uname:

Linux mavtest 2.6.32-21-generic #32-Ubuntu SMP Fri Apr 16 08:09:38 UTC 2010 x86_64 GNU/Linux

current uname:

Linux mavtest 5.4.0-31-generic #35-Ubuntu SMP Thu May 7 20:20:34 UTC 2020 x86_64 x86_64 x86_64 GNU/Linux
New About to punt
do-release-upgrade stalls on building data structures. Updating the sources and update/upgrade stalls downloading a source. If I can track down where that source is and disable one repo I'll try again, otherwise I'm going to do a fresh install.
--

Drew
New What's in the logs?
New Wood. HAAAAAHAHAHA!!!!
Actually I haven't had time to mess with it today. Might try tonight.
--

Drew
New Nothing useful
I was about to start a clean install, but it indicates you need 2 Ghz dual-core and 4G RAM to run the default (Gnome) desktop. This box is far short of those specs, and I don't trust the installer not to brick it. Besides, I *like* the current desktop on this thing. Now I'm thinking I'll just keep it disconnected from the net, do the book updates I want, then wipe and get rid of it.

My inner nerd is screaming at me to not let this hunk of metal beat me. My inner adult is telling my inner nerd to piss off.
--

Drew
New OS/2 is Old!
Dumped it (well - sort of) a couple of years ago. My two former OS/2 computers (my two main computers) now run ArcaOS - the 2017 update from OS/2.

Only problem I have, the running version of Firefox is pretty long in the tooth, I couldn't get the Firefox beta to run (thought other people have). Firefox development has pretty much stopped, and the promised Falkon browser (in active development) isn't quite finished yet. Porting all the libraries from Linux has been the problem.
New Progress! I think ... maybe
I had tried all the Ubuntu graphical package tools, and the command line. On a whim I tried Synaptic. I watched it fail to pull the translation files - which is what kept stalling the command line update - but get everything else. I kicked off a dist-upgrade before heading to bed.
--

Drew
New I have had some success with Aptitude for apparently-borked apt issues
New 2nd this
The interface can be rather infuriating but you get a good view at what is broken/stuck. And it groups the packages so you can deal with one area at a time.
     How to update really old Ubuntu install? - (drook) - (39)
         what happens when you use wget to get that file? -NT - (boxley)
         Don't go straight from $ancient_version to $modern_version, if possible - (pwhysall) - (14)
             Working, please wait... - (pwhysall) - (13)
                 You must be bored, but ok and thanks - (drook) - (1)
                     Well, that's Linux for you :D - (pwhysall)
                 I noticed - (drook)
                 So, it works. - (pwhysall) - (9)
                     About to punt - (drook) - (8)
                         What's in the logs? -NT - (pwhysall) - (7)
                             Wood. HAAAAAHAHAHA!!!! - (drook)
                             Nothing useful - (drook) - (5)
                                 OS/2!! - (Another Scott) - (1)
                                     OS/2 is Old! - (Andrew Grygus)
                                 Progress! I think ... maybe - (drook) - (2)
                                     I have had some success with Aptitude for apparently-borked apt issues -NT - (pwhysall) - (1)
                                         2nd this - (scoenye)
         What's the toolchain you're trying to resurrect, btw? -NT - (pwhysall) - (19)
             LaTex / Lyx plus several plugins for formatting -NT - (drook) - (18)
                 Can't just lift config and make files? - (pwhysall) - (17)
                     I set it up (apparently) 10 years ago - (drook) - (16)
                         Let a lazy bastard help - (pwhysall) - (15)
                             Lyx / LaTeX doesn't fail so usefully - (drook) - (14)
                                 I had an old PC act up recently... - (Another Scott) - (13)
                                     PS/2 keyboard works, but ... - (drook) - (12)
                                         Also... - (pwhysall) - (11)
                                             Maybe once I drop the coin on a new box - (drook)
                                             This^^^^ - (crazy) - (9)
                                                 Ok, so how? - (drook) - (8)
                                                     It's been years for me since I've done this stuff - (crazy)
                                                     If possible choose default instance environment. - (crazy)
                                                     Re: Ok, so how? - (pwhysall) - (1)
                                                         Nice. Thanks for the pointer. - (Another Scott)
                                                     2) depends on your current active kernel - (scoenye) - (2)
                                                         May not matter, I believe I've bricked it - (drook)
                                                         10.04 works like a dream in VirtualBox - (pwhysall)
                                                     Just came across this - (crazy)
         Turns out there was an easy solution - (drook) - (2)
             Neato. - (Another Scott) - (1)
                 On running hot - (scoenye)

I bumped into a dot.
102 ms