Transferring user data from a Mac to a Windows PC can be problematic. This short post describes some of the problems you will encounter.
This post also describes the best way to transfer POP3 email from Mac Mail to Outlook.
Mac Address Book contacts are perhaps most problematic of user data that needs to be transferred and they are discussed in another post.
The first and most problematic issue is that file name length (pathname + file name) can exceed 255 characters in OS X with no issues. Windows, however, has a 255 character limit on file name length. On the Mac side, copying to an external FAT32 drive is not a problem. All files are copied successfully, including those files with pesky long file names. On the Windows side, however, transferring files with names over 255 chars to Windows is impossible using drag and drop from the external drive. The copy will just stop at the first occurrence of a long file name.
The only way to solve this length issue is to delete or rename each offending file on the external drive before the drag and drop. A program such as the utility found at http://longpathtool.com can help find and delete these files. They need to be renamed (as opposed to deleted) as I have to assume they are important to the owner and as a computer tech, I don’t have the time to ask the owner about each file. So I rename them. Often shortening one of the sub-folder names will fix the problem without renaming the file itself.
The second issue is about all the “junk” files that OS X creates, usually beginning with a period. .DS_STORE is just one example. Another is files beginning with “._.”. These are hidden from the user on the Mac, but quite visible on the Windows side. These all have to be removed as they serve no purpose on Windows. Not especially challenging but somewhat tedious.
Regarding POP3 email on Mac Mail, the goal is to transfer all email messages (and attachments) in all folders and sub-folders to Outlook, and preserve the sub-folder structure. After researching this at some length, I concluded that a commercial product could achieve this with much better precision, and much quicker, than any roll-your-own method. The product I used is written and sold by Gladwev Software Pvt. Ltd. It’s called “Apple Mail to PST Converter” and I must say it is easy to use and works like a charm. On the Mac, it creates a Windows Outlook PST file containing all messages and attachments, and preserves all of the sub-folders. I then transported this PST file to the Windows PC and started Outlook, and then imported all the data in said PST file. It worked perfectly.