Catalina Upgrade vs Clean Install

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Are there any situations whereby a clean install is better than an upgrade? I ask this because I did clean install on my MBP without issue; but my MBP doesn't have all the files on it that my iMac has. So this was relatively straight forward. Next on the list is my iMac. What worries me the most are the mail boxes I've created that are stored "On my Mac" as opposed to iCloud. If I did a clean install of Catalina on my iMac I know I can import/restore all of my Documents from my Time Machine Back Up but can I do the same with the mail folders? If there's anything you think I'm missing please feel free to let me know. Any advise and help will be greatly appreciated.

Thanks,
Mike
 
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When I did an upgrade, I ended up with a folder "Relocated items" on the Desktop. So I did a clean install a week later.

I don't like having email folders only on my Mac. I prefer to have the email, whenever I need them, wherever I am.
 

chscag

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Any advice and help will be greatly appreciated.

I would do the upgrade first. If things don't work out, you can always back up and do a clean install. A clean install can be easy or it can be daunting depending on what you need to restore after the clean install. And as far as the "relocated folder" which may appear on your desktop, that's easily taken care of. Lots of threads about it. I just deleted it without any problems. It is after all just a copy or alias.
 
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When I did an upgrade, I ended up with a folder "Relocated items" on the Desktop. So I did a clean install a week later.

I don't like having email folders only on my Mac. I prefer to have the email, whenever I need them, wherever I am.

Thank you, much appreciated. :)
 
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I would do the upgrade first. If things don't work out, you can always back up and do a clean install. A clean install can be easy or it can be daunting depending on what you need to restore after the clean install. And as far as the "relocated folder" which may appear on your desktop, that's easily taken care of. Lots of threads about it. I just deleted it without any problems. It is after all just a copy or alias.

The upgrade is my first option. The only issue I encountered during the clean install on my MBP was that iCloud Drive got turned ON. Turns out I got momentarily confused between iCloud and iCloud Drive. I resolved this by going into my Apple ID and turning OFF iCloud Drive. Other than that everything else went smoothly.
 
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You can have iCloud Drive "on", you just want to make sure "Desktop & Documents Folders" is not enabled.
 
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You can have iCloud Drive "on", you just want to make sure "Desktop & Documents Folders" is not enabled.

Yet another good point I hadn't thought about ... thank you once again. :)
 

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