This right here. This is why I bought all the JetBrains IDE's as a personal license, aside from my student graduation discount, all these IDE's allow me to be seriously productive at work. I do not regret buying JetBrains at all, had it been a thousand dollars I would of probably have thought twice, but the value it returns to me is worth it honestly. I'm definitely more productive with the JetBrains toolset.

Exactly the same for me. Although I do not use all tools at the same time, I still feel the money was worth it.

I have thought to do the same with Visual Studio, but VS Community Edition + ReSharper is basically VS Ultimate.

For HexRays... Its a really high price, and its software I don't make full use of, so i just keep working on the older, leaked versions instead.

I don't use every tool, but I still find it worth it. I mostly use PyCharm, WebStorm, DataGrip (if you do any SQL work give it a try!) and of course ReSharper. I don't see Rider as "ready" yet, seems to not support opening up some of my .NET Core solutions still. Hoping it becomes stable and usable like regular VS.

Another category is audio software plugins (aka VSTs / AudioUnits), which are sometimes sold in bundles of $1000 or more. The plugins often cost more than the software that runs the plugins. Take a look at the Waves bundles:

https://www.waves.com/bundles#sort:path~type~order=.hidden-p...

Or some of the iZotope products:

https://www.izotope.com/en/products/repair-and-edit/rx-post-...

Certainly many of their customers are recording studios, but a lot are individuals. If you're a voice-over artist or producer, you probably don't mind spending this much if you're making money with it and it saves you time. If you're a professional, you're probably spending $1000+ just on a microphone anyway.

That makes sense. But why that? It seems like it would make a lot more sense to market to hobbyists, of which there are a lot more of (as jetbrains and newly adobe have done), or to large companies which will pay a significant sum to give all their employees access to the software.

Matlab/Mathematica and its ecosystem of plugins as well.