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I've decided I want to take the plunge and leave Gmail for Mail, using my iCloud account. Why? I've lost trust in Google (incl. their search bias, how they handle my privacy, and how they treat the end-user as a comodity to sell rather than a customer to serve). I know there are others like me (I just found today: www.leavegooglebehind.com)

I'm looking for answers on how to swap over completely from Gmail to Mail while retaining the functionality I'm accustomed to. I've done a bit of researching and can't seem to nail the answers to my questions. Your answers on any of the items below would be much appreciated. And if you think there's a better way I should be asking the question, please let me know.

Here's what I'm looking for especially:

  1. I use Gmail's labels a lot. How can I get the same effect in Mail? Smart folders? (I do wish smart folders synced to iCloud.) Note: I am not asking about replicating + maintaining Gmail labels in Mail — I don't need to replicate + maintain: I'm leaving Gmail. I just need a system with a similar functionality. Something I could use on both my Mac and my iPad would be ideal.
  2. I have a lot of Gmail labels. What's a good way to export from Gmail without getting oodles of duplicates? Forwarding folder by folder would be time consuming + lossy, and stripping the labels would be counterproductive. Are those my only real options? Note: Yes, I know this question does get attention, but a lot of the attention is quite old. Both Gmail and OSX have changed a lot over the last few years. I'd love a good recent resource, based on Lion + Mt Lion.
  3. I use a lot of Gmail filters. Mail rules seem even better, but is there any way to automate transferring my filters to Mail?
  4. I use Gmail 'send mail as' with a collection of non-gmail addresses (from my domains). Is there any way to use my iCloud account to send from a non-iCloud address? Or, is my only option to sign up with a different webmail service in order to send from my alternate addresses in Mail?
  5. Like many people, I have my own set of pre-defined Gmail keyboard shortcuts. Do I just need to tough it out and learn the Mail shortcuts, or is there a good, free/inexpensive app for adding shortcuts to Mail? And no, I don't mean through SysPrefs (I know how to do that ;) ). I mean Gmail style single-letter shortcuts, like 'r' for reply.
  6. Tips for converting Gmail Contacts to Address Book. Note: This area also gets some attention, but again the attention I keep hitting is old.

If you've made the switch, I'd be especially interested to hear your experience! I'd really like to get Mail up and running sooner and rid myself of Google.

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Are you using Apple's mail app for both accounts now, or are you using gmail's web UI? I use mail.app for both a gmail and .me account and while I shunned mail.app for a number of years, preferring Sparrow I've moved back and I'm happy I did. I've considered slowly moving away from gmail too but for me it's been much more reliable and faster on all devices than my .me (Apple) account. So, I'd test both for a while in mail.app before you cut the cord. –  Richard Nov 6 '12 at 12:24
    
I think it will take adjustment for you. Mt. Lion still doesn't have labels, so folders are the next best thing. I personally think it would be best to learn the default keyboard shortcuts for Mail.app. They really are very logical. I.e. Cmd + N, for New Message, and Cmd + R, to reply, etc. I'm not aware of any way to automatically transfer filters. I'm sure that will have to be done by hand. Like @Richard, I also use Gmail in Mail.app, and like it. One thing you will likely find helpful is to bring Gmail into Mail.app. At that point you can copy any Gmail files over to .me, as well as emails. –  bassplayer7 Nov 6 '12 at 13:59
    
I can not fault your sentiment at all. Gmail works though. That's the thing, because your data is gonna get sold regardless. Google does not care what you do as long as you look at the ads. Apple wants to control the user experience. Gmail does work well though. –  chiggsy Nov 6 '12 at 17:03
    
@Richard - I'm using Mail just for my iCloud account. Yes, Gmail is more reliable and faster. If Gmail were made by anyone else, I'd hold on to it. It's one of my favourite apps. –  Fire and Mirth Nov 6 '12 at 20:23
    
@Bassplayer7 - I've synced Gmail completely with Mail in the past, but because I have so many labels, and because Mail can't do labels, my computer suffered appreciably. I'm wary to do that again. I'd rather solve how I'm going to handle labels before I start bringing my messages over from Gmail. –  Fire and Mirth Nov 6 '12 at 20:27
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2 Answers 2

I think it's safer to just stay with Google Mail. The Google Drive Integration is amazing and lets you share files seamlessly across devices just like DropBox.

Now they are giving away 15GB space for your email (from Google IO 2013)

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Before you completely ditch GMail and go just with your iCloud account, you'll need to ask yourself this question:

Will you only access your mail solely from Apple devices?

I for one created an iCloud e-mail account on my Mac just to be disappointed that I couldn't configure my Android phone to access it. Probably Apple is not using standard IMAP for its iCloud e-mail service.

That said, you could upgrade your GMail account to a premium account to get better quality of service (and perhaps not having them selling off your e-mails).

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I don't think Gmail supports premium without changing your e-mail address. –  Erik Allik Dec 6 '13 at 3:48
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