Hi,
I am new to this forum so apologies if this topic has already been answered. I looked around but could not find any information.
I have 2 questions:

Background
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I am using Media Monkey Windows Gold version 4.1.23.1881 on a Windows 10 Acer Aspire S3 laptop.
I have a music database of approximately 5400 songs.
Copying the music files using MMW with my FiiO X3 worked without any issues.
However, when trying to copying the same music files to my iPod Classic 160 Gb it does not seem to work.

My Problem
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When I copy about 500 songs then eject my iPod, I can see the songs on my iPod without any issues.
However as I add more and more songs there is a random point (generally above 1000+ songs) when suddenly, either:
1. after I safely eject my iPod, the iPod says there are no songs, although when I look at the hidden music folders on the iPod the song files can be seen under the usual iPod_Control\Music\F00...F49\ folders which I can play directly by double-clicking on the file under Windows.
or
2. I cannot eject my iPod as the MMW says iPod is in use and I can never clearly eject my iPod.

I have tried to shut down the laptop so that I can eject my iPod but every time I do this, the iPod says I have no music so I am assuming the iTunes database on my iPod is corrupted even though there are many music files on the iPod. As I cannot find a way to correct this issue without re-initializing my iPod, I am quite frustrated.

I have completely reformatted, then re-initialized my iPod using iTunes 10.x before connecting to MMW for the music transfer to my iPod Classic 160 Gb but it never seems to work. This has now been repeated several times with no success on several different computers.

Question 1:
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What am I doing wrong? If the process works with my Xiio X3 player, why does it not work with my iPod Classic?

Question 2:
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I tried to use the synchronization function of MMW but I am not sure if this is working or not as all I can see on the MMW status bar is "Synchronizing iPod: (Preparing list of files)" and then seeing on my iPod the rotating arrow appearing fromm time to time to I assume show that something is happening on my iPod.
This has been going on now for over 5 hrs I am starting to wonder if maybe I am in an enless loop or something.

My question: Is there any way to have a more active feedback as t what is exactly happening during the synchronization process e.g. show what files are being copied, what files compared etc. so that at least we know it is working correctly and I know that I just need to wait until it is over.

Thank you in advance for any advice.
Cheers