Re: I'd like a pony with that one, please
To be fair, he's talking about the cases I mentioned where the people packaging their proprietary application didn't package it properly, so it's not hooked into the dependency system, so it doesn't know what 32 bit libraries it needs, so the user needs to do a web search, type a 30 character command, and wait 15 seconds in order to compensate for the developer's poor understanding of the OS.
The equivalent, of course, being the much more commonly encountered "DLL hell", where you download some random exe from the internet that isn't bundled in an installer, and after you've scanned it for viruses, and then scanned it for spyware, and then you scan it for malware which is triggered because the person who wrote it used a .net obfuscator because for some reason they think the source to their tiny little utility is somehow precious and needs to be secret, so you have to investigate that and decide whether you think it's safe or not, but the guy didn't even publish an MD5, let alone a SHA, let alone an SHA256, so you can't even checksum it, even if you do happen to have an MD5 tool that wasn't included as part of the default OS install for some reason. And then if you decide that's OK you run it through another different virus scanner just to be safe, because two is better than one amirite? But the second scanner actually already scanned it because it's a resident scanner that scans every file on access, slowing down all file access on your machine, even for non-executable files like jpegs, but you don't know that and even if you do, scanning everything you download is just habit now. So then you try to run it (without the need to mark it as executable, because, hey, if it's named ".exe", it's just executable! But you don't actually know whether it's executable or not because windows hides file extensions by default. So just double-click it, what's the worst that could happen? This isn't a security problem at all!). After you've done all that, you get a message saying, in its entirely, in a dialog you can't copy the text from: "GEADYSC.DLL not found". And so you go to the internet and download GEADYSC.DLL from some totally-not-dodgy russian site. And you run that through all your scanners, and you copy it into the windows system directory, which requires elevating your privileges. And then you run your exe again and get, in its entirely, in a dialog you can't copy the text from: "wrong GEADYSC.DLL version". With no information on what version it actually wants. And that's if you get a descriptive error message and it's not something more cryptic like "GEADYSC.DLL: invalid entry point for call 'AlertUserAboutWannaCryRansom()'". So you just start downloading random versions from random totally-not-dodgy-russian websites, and running them through all the scans, and elevating your privileges so you can copy them all into the windows system directory, and just repeat the process over and over until one version works, hoping that the malware warning triggered earlier was just a .net obfuscator and not actual malware. All because you wanted to run a keygen for software you couldn't be bothered investigating free alternatives to.
And that's assuming you're lucky, and some program you use all the time doesn't need a different, incompatible version of GEADYSC.DLL and you just broke the other program. And that windows didn't complain loudly when you copied the version you wanted into the system directory and then silently restore the file the next time you reboot (i.e next time you need to change your desktop wallpaper, or sneeze too loudly, or when the wind starts blowing north-north-west. Either way it's going to be less than 24h later).
And that's also assuming that the 32 bit program you're trying to run wasn't built for Windows 95, in which case the dialog will say "We couldn't be bothered making our OS compatible with itself. Eat a dick". But to be fair that IS a much simpler situation with much less faffing about than DLL hell.
So, yes, there are occasionally hurdles to getting a 32 bit program working on Linux. If the people distributing that software haven't packaged it properly.
But I'm still yet to see anyone address how well current windows versions run games built for Win95. I guess things must have changed since the last time I used windows and there's no tinkering or tweaking or hurdles required to get, say, a great old game called Stratosphere running on windows 10.