IPod Sync problems / Backup advice needed

A few months ago I had some kind of crash in iTunes and lost all of my playcount information. Fortunately I was able to restore most of what was missing by backing it up from my iPod, but as my iPod was set to auto-sync at the time, I had to connect it and quickly block the auto-sync and set it to manually update (I can't remember exactly what key combination makes this happen, but a very kind person on here told me about it and I don't have the hyperlink to hand at the moment).
The problem is that now I want to set it to auto-sync again, but whenever I go into the settings and uncheck the "Manually manage playlist" option and hit Apply, it automatically rechecks the box and doesn't accept the changes. Does anyone know how to get around this?
Also, my computer is getting sluggish and basically needs a complete rebuild soon. Can anyone advise me on the best way to back up all of iTunes, including my library and all of the playcount information?
I'm a Windows user, if that makes any difference. Many thanks.

Hi E4monn,
It sounds like you can see all of your music purchases in iCloud but they are not syncing from your Windows computer to your iPod. In this situation, I would recommend making sure that all of the music you are trying to sync has been downloaded into your iTunes library prior to syncing. Please reference the Download previous purchases on Mac or PC section of the attached article to download all of your purchased music to your computer. 
Download past purchases - Apple Support
Have a great day,
Joe 

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