But, will I be able to select i.e. four objects and enter Sculpt mode with only two of them, while the rest fo those four objects will still be selected?
Yes, because while you are in Sculpt Mode, you can still select other things in the Outliner. You can also pull objects into the current mode session, which were not selected when you entered the mode.
No, I can’t - selecting other object while I’m in Sculpt mode turns me back to Object mode. This only makes sense, when selected objects are added to current Sculpt session, or switch Objects I’m sculpting. Nothing like that happens.
Man, what’s the purpose of selecting things, that I don’t work on at a moment?!
By the way - selecting thing in Outliner is a hell of mess. Nothing works, as expected. Some data is clicable, end enters edit mode, other does not…
You’re describing a situation like this one basically?
From what I understand from your previous posts, you would like to also have the ObData of the Cone highlighted, in a different way, but I can’t get why.
I’m getting a bit confused about this, to me it only makes sense to highlight the object data when the related object is in edit mode as it is now, then whatever one selects in the outline should be communicated highlighting the row, as it is now.
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@a.monti Regarding second part of Your post - that’s exactly what my mockup depitcs.
Outliner should be straightforwadrd in use, without cumbersome confusing states. No one uses Outliner without 3D View, which clearly enoug communicates which mode is on the fly.
Why, I always wondered? When I click an object it turns to edit mode. But when I click on a material icon or a modifier icon, nothing happens. Can this be changed?
It would be nice if I (double) click on a material in the outliner, the menu below opens up right away. Same for the modifier icons. This would safe so much time searching and fiddling around. Same for lights, camera, etc
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There are many more.
With an Object selected, one can double click on its ObData and Blender triggers the Edit mode (in 3D View!). Then it’s possible to add to the current Edit mode session or remove others Objects ObDatas by clicking them in Outliner. But after a user is back to the Object mode, it’s impossible to enter the Edit mode with other ObData just by clicking them in Outliner. One has to select Object in 3D View first, then double click its ObData in Outliner. Or better hit the Tab 
Totaly counter intuitive.
It’s a topic for another conversation though.
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Exactly! It is absolutely counter intuitive. Should this be adressed? Can we make a proposal or something? Or is everybody fine with the current behavior?!
I’m not. Overcomplication and lack of intuitive usage patterns- to me this is main reason to not use Outliner at all.
Yes, that’s what I thought at the beginning, then at some point I completely lost the thread. 
Using an app should be straightforward and intuitive on a basic level. Steve Jobs knew that well and that’s why his products were so good.
Outliner is just a part of Blender and deffinitely doesn’t have to present all information of what happens with a data block at the moment. To get complete info of what’s up, a user has to pair it with 3D View or other editor. It’s like an analogue library catalogue - it collects and shows some info about library’s content - what’s a book’s title, who wrote it, where to find it. But to get more detailed info, You shall go to librarians desk, he/she’ll present You more details - is the book loaned, how many people had it read, what colour is it…
Number of information within Outliner is limited and it must stay like this. You click a data block and You instantly edit it in another part of the app - in an Editor. The very Editor clearly shows the mode. No need to reflect it in Outliner. Moreover, adding things to selection in Outliner, must add the selected data to current mode in Editor. Selected=edited. ObData has just two states form Outliner’s point ov view - it’s edited or not edited. Oject data block is editable always when selected, but can be active at the same time or not. For time being most editors affects only Active Object, but after MultiObject editing will be completed, things will change and I propose renaming the Active Object to Last Selected.
my usual 2 cents …
I take this opportunity to point out that this area is a very useless waste of space that could be revisited in a better way
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That’s how I imagine what @billrey states for:
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Nothing selected
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One of Objects is chosen. It’s Active and in Object Mode/Sculpt Mode/ Whatever Paint Mode. Generally speaking in every mode with exception for Edit Mode. All bined data blocks are highlighted as well, but their look shows, that they’re not under edition now.
I don’t really know what should Material look like, since it has no edition mode at all, but currently Outliner higlights the material bined to Actove Object, do did I.
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The same with multiple Object selected.
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Mesh ObData is double clicked - Edit Mode triggers.
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The same with multiple Object selected.
Have a couple of remarks about Material Data - does it have a corresponding edition mode? No idoesn’t but it can have one. Double clickingin could throw a User into Shader Editor. Bam, and highlight style changes the way it does with Mesh ObData Edit Mode. Besides - how will it handle Multi Object editing?
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candy crush Outliner?..
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Something like that could work, I think. Question: why is the first Object highlighted when it’s not selected?
How so? In what way could it be better?
So, highlithing a row in Outliner is impossible without selecting a data?
I thought that those are separate things - data blocks and outliner rows. Maybe that’s the reason for our misunderstanding?
If so, could one of states go away, like in my previous mockups, with the row higlighting corrected?
I’m not completely sure what you are saying. Datablocks and Outliner rows? All the rows in the Outliner are datablocks
You seem to have two types of highlighting, and I don’t understand exactly what is going on there.
The whole thing with selecting and highlightning in Outliner is confusing as hell. At least for me, which isn’t a good thing, since I’m ought to propose You a hint of a design of colour and icon use.Things are higlighted in an unpredictable way. Higlights in Outliner does not have reflection in 3D View and vice versa. Total mess it was and it still is. I tried to sum up its actions, but I gave up for the reason of so many combinations possible. The whole thing is functional grotesque in my eyes.
For instance - clicking on rows in Outliner adds Objects to selection in 3D View. Then I can use A-key shortcut in 3D View - all Objects are selected in 3D, in Outliner icons are highlighted, but no row is selected. After deselection in 3D View (double A-key), I go to Outliner and tap A-key - all rows are highlighted, but no Object is selected in 3D View. But when I click a row in Outliner, the very row is highlighted, Objetc’s icon in Outliner gets highlighted and the object in 3D is selected. Clicking on an object in 3D View highlights proper Object’s icon in Outliner but not the row, moreover previously highlighted rows stay unafected. No consequence. No sense.
I’m totally confused…
You’re also lost, even though all I’ve done is a simple reproduction of the snaphot of a real Outliner but with different visual style/accents. Looks like my previous mockups were somehow valid. This one is too:
It shows a common situation - a state of Outliner, that I can easily recreate. Here’s the proof, a screenie:
Both - my mockup and the screenshot - depict real state of Blender’s Outliner, but it seems that nobody understands what’s happening there, and why things are highlighted. It means that the design is broken from scratch.
I give up - can’t work on a thing that I don’t understand. Unfortunately I have neither free time nor free resources to dig into it as deep as it deserves - simple colour coding won’t fix it.
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I don’t like those colored sprinkles. Would it be possible to just highlight the text and icon without that color capsule?