How can I leave Gmail for Mail?

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 commodity 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.

Solution 1:

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).

Solution 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)