Apple/Microsoft Compatibility

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I have an ageing iMac (Build 10,10.5 running Yosemite) which I might add is still operating OK. The problem is that Apple in their infinite wisdom No Longer support it, I cant upgrade from Yosemite and since Google Chrome updated their system my iMac Apple Mail cannot interface with GMAIL.
This prompted me to buy a HP laptop running Microsoft Stuff. I investigated the transportability of iMac documents files to a Microsoft device before purchase and was advised that there was NO PROBLEM with transferring these files. Oh how wrong that is. In the years I have used Apple Documents as a means of storing all sorts of document files, I have never even considered what Apple did with respect to file extensions. When I tried to transfer the Apple Documents folder to the Microsoft HP laptop, all of the files were successfully loaded into the Microsoft Documents folder. I was elated until I discovered only about 10% of the files were readable by the Microsoft system. Looking closer the file extension on 90% of the files were not recognised by Microsoft. I could get some success if I took an unrecognizable file on the iMac and exported the file using one of the available selections. This was reasonably successful in that Microsoft could 'See' it but displayed it but was not the same as the original file.
So the information I had before embarking on this switch to Microsoft was totally wrong and the thought of taking every file in my iMac and re exporting it in another file format fills me with horror.
So the point of my posting is that has anyone any suggestions of overcoming the document file transfer issue of Apple to Microsoft.
Treat me gently if you reply to this posting, I am not an expert on these issues, I can just about spell Microsoft with a bit of effort.
 
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I run Office 365 on my MacBook Pro (which is relativly new.
Have you tried using Open Office as a translation tool.
 
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Thanks everyone for your help. I have had no success what so ever with this Windows11 System.. I am going to give the Laptop a new home with someone who can drive it.
 
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