I think that two criterias are important:

- don't block my productivity
- author should have his userbase in mind

1) Some simple anti examples:

- Windows popping up a big fat blue screen screaming for updates. Like... Go suck some donkey balls you stupid shit that's totally irritating you arsehole.
- Graphical tools having no UI concept. E.g. Adobes PDF reader - which was minimalized in it's UI and it became just unbearable pain. When the concept is to castrate the user in it's abilities and call the concept intuitive, it's not a concept it's shit. Other examples are e.g. GEdit - which was severely massacred in Gnome 3 if I remember correctly (never touched Gnome ever again. I was really put off because their concept just alienated me)
- Having an UI concept but no consistency. Eg. looking at a lot of large web apps, especially Atlassian software.
Too many times I had e.g. a simple HTML form. In menu 1 you could use enter. In menu 2 Enter does not work. in another menu Enter works, but it doesn't submit the form it instead submits the whole page... Which can end in clusterfuck.
- Keyboard usage not possible at all.
It becomes a sad majority.... Pressing tab, not switching between form fields. Looking for keyboard shortcuts, not finding any. Yes, it's a graphical interface. But the charm of 16 bit interfaces (YES. I'm praising DOS interfaces) was that once you memorized the necessary keyboard strokes... You were faster than lightning. Ever seen e.g. a good pharmacist, receptionist or warehouse clerk... most of the software is completely based on short keyboard strokes, eg. for a receptionist at a doctor for the ICD code / pharmaceutical search et cetera.
- don't poop rainbows. I mean it.
I love colors. When they make sense. but when I use some software, e.g. netdata, I think an epilepsy warning would be fair. Too. Many. Neon. Colors. -.-

2) It should be obvious... But it's become a burden.

E.g. when asked for a release as there were some fixes... Don't point to the install from master script. Maybe you like it rolling release style - but don't enforce it please. It's hard to use SHA256 hash as a version number and shortening the hash might be a bad idea.

Don't start experiments. If it works - don't throw everything over board without good reasons. E.g. my previous example of GEdit: Turning a valuable text editor into a minimalistic unusable piece of crap and calling it a genius idea for the sake of simplicity... Nope. You murdered a successful product.
Gnome 3 felt like a complete experiment and judging from the last years of changes in the news it was an rather unsuccessful one... As they gave up quite a few of their ideas.

When doing design stuff or other big changes make it a community event or at least put a poll up on the github page. Even If it's an small user base, listen to them instead of just randomly fucking them over.
One of my favorite projects is a texteditor called Kate from KDE.

It has a ton of features, could even be seen as a small IDE. The reason I love it because one of the original authors still cares for his creation and ... It never failed me. I use Kate since over 20 years now I think... Oo

Another example is the git cli. It's simple and yet powerful. git add -i is e.g. a thing I really really really love. (memorize the keyboard shortcuts and you'll chunk up large commits faster than flash.

Curl. Yes. The (http) download tool. It's author still cares. It's another tool I use since 20 years. And it has given me a deep insight of how HTTP worked, new protocols and again. It never failed me. It is such a fucking versatile thing. TLS debugging / performance measurements / what the frigging fuck is going on here. Take curl. Find it out.

My worst enemies....

Git based clients. I just hate them. Mostly because they fill the niche of explaining things (good) but completely nuke the learning of git (very bad). You can do any git action without understanding what you do and even worse... They encourage bad workflows.
I've seen great devs completely fucking up git and crying because they had really no fucking clue what git actually does. The UI lead them on the worst and darkest path imaginable. :(

Atlassian products. On the one hand... They're not total shit. But the mass of bugs and the complete lack of interest of Atlassian towards their customers and the cloud movement.... Ouch. Just ouch.

I had to deal with a lot of completely borked up instances and could trace it back to a bug tracking entry / atlassian, 2 - 3 years old with the comment: vote for this, we'll work on a Bugfix. Go fuck yourself you pisswads.

Microsoft Office / Windows. Oh boy.
I could fill entire days of monologues.
It's bad, hmkay?

This is not bad.
This is more like kill it before it lays eggs.
The deeper I got into XEN, the more I wanted to lay in a bathtub full of acid to scrub of the feelings of shame... How could anyone call this good?!?????

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    I'll call myself lucky to have skipped over Xen - I fell in love with Qemu and KVM ... or rather with Libvirt and virt-manager. And I get what you mean with Atlassian - been there, done that... when you actually use their products you start running into things just plain missing and then tracking down three f**king different bug tickets or just feature requests from three different time periods!

    Also Kate = ❤️
    It's steadily becoming my go-to editor for anything starting from notes to scripts and large configs.
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    I work in a non IT company and not as a dev but I do write code (long story). Since our software we are able to install is curated, only Kate was available as an "IDE". Ive grown to like it very much. Fortunately for the Java code I have to write I can use IntelliJ. We had IBM ODM before, an Eclipse based Business Rule Engine and it was all the ba
    D stuff from Eclipse somehow made worse; The deployment was done via an interface that requires Internet Explorer. It didnt work with anything else.

    As for git GUIs, we work with TortoiseGit since non tech people have to use git (as I said long story) and TortoiseGit is... Easy enough to understand and not fuck up completely. Since all we have to do is push to a sandbox where everything is screened by someone who knows his stuff and deployed to production from there, therefore learning git beyond commit/push isnt necessary, having a GUI is kinda nice.

    Company recently migrated to Microsoft Office 365 and its been a complete clusterfuck.
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    I have honestly never seen anyone shit on Gedit and praise the usability of git cli in a single post lol. Kudos.

    I would love to use kde stuff.. if it didnt install all the kde stuff in the world just for an editor. Also some people like minimalism. Like me. But gedit still cut it. I would much rather use vscode / sublime than gedit.
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    Really like gnome 3, joined the party late so perhaps not seen the early fails.

    I was wondering why I couldn't find a lot of settings or things that I used to do with gedit. You are right they completely fucked it over. Kate used to be my go to editor a long time ago. It was awesome. I was on Gentoo and most applications I used where GTK so dropped it as gedit was fine too and not compiling Qt saved a lot of time.
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    @purist I was in the same boat when I was on GNOME... I still like it, but I can't live without tweaks and extensions, which, keep breaking all the time between updates. For a while, I even had both GNOME(as main DE) and KDE(as fallback and to gain access to KDE apps) installed but eventually just switched over to KDE and permanently said goodbye to an extension or two, for which there was no equivalent replacement in KDE.
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    @theKarlisK Oh.. I also ditched gnome.. not because of the problems you are saying. But because i thought it was too heavy for my comfort. I am with xfce for more than 2 years and i am very happy inspite of minor issues with some programs.
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