Transfer between iPod and iTunes - mission impossible !

I recently got iPod Touch (latest model with latest iOS) - just to use it in my car. I simply wanted to add and remove few songs. In a normal world, there would be just 2 columns (ipod/computer and simple managing both parts within files and folders management - let us be sincere, can anything be more natural and straightforward ? Sure not). But Apple wants it to make super complicated and highly frustrating. OK, what to do,
Since I already have a different computer (newer version of MBP Retina, with the latest OSX) , I needed to get the iPod content to the iTunes on the new computer somehow. This is impossible as such - since iTunes keep telling that if I want to associate this iPod with this iTunes library , I have to erase the iPod (this is something I really don't want). I try "full backup" - as offered by iTunes ... I do it few times, the process starts, but always lasts quite short (considering 1700 songs with 24 GB on my iPod). The result is - nothing is backuped to this computer ... very nice ...
In further search, I discover some third party apps, that supposedly could help with this terrible process. I bought AnyTrans and started transferring the content to iTunes. in 9 hours, it was just 4 GB transferred ... (overnight) ... obviously not the way ... On another advice , I bought iExplorer, it should be supposedly better. I tried to transfer the iPod content to iTunes ("start automatic transfer). I tried it 5 times. As a result, the app always froze and for quit was the only solution. NIce. Then I got an advice that it is good not to transfer to iTunes but just to some folder on a computer. That finally worked. Good
Then I added all these songs to iTunes Library (finally some first result after many hours of effort). Then I agreed that this iPod can be associated with this iTunes Library (that already contained those 1700 songs) and let it synced with this iPod.  After some time the iPod was indeed erased. No music in it any more. As much as I tried again and again to sync it with iTunes Library, the process went in three short steps and finished. The result - no music on iPod, whatever I do ... Full music Library in iTunes on MBP
What shall I say and still keep my expressions decent ? (difficult) This iTunes and this system of working with files on iPod or iPhones is for me the most stupid invention ever. How could someone ever create such a terrible nonsense that make simple things impossible and highly frustrating ? Instead of simple file transfer between devices ... I have no words for that ... It is also possible that it is me who is stupid, in that case, please let me know how can I transfer songs from iPod to iTunes and how can I how some songs on iPod (that are already in iTunes Library). Not to waste computer space by having iPod library copied there, is another thing, but let us not go to details now

Yes, all played in iTunes in the computer, right boxes checked (see the printscreens) ...  In the end , I restored to restarting iPod and MBP. After that it started working (synchronisation). But only up to some extent. In iTunes Library I have about 1700 tracks, but only 660 were transferred to iPod. Now I made: "add to library" - adding to library all the song I already have in Library: and the iTunes started working hard to add the rest in the Library (but they were already there ...)
So finally I spend nice whole day to add/remove songs in my iPod ... 
Another thing is - when in iTunes Library I want to add/change genre to some songs, the process takes so long, it is like each song is freshly copied just to add the tag "classical" etc to each ... I thought I have the "fastest Mac ever" ... Waiting so long for such trivial process is unbelievable ... (with rainbow circle making a nice decoration now and then)

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