How best do I leave Gmail for Mail?

Question

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'd love advice on the best way to swap over. I've done a bit of researching and can't seem to nail the answers to my questions. Your help + advice 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:
I use Gmail's labels a lot. What's the best way to get the same effect in Mail? Smart folders? (I do wish smart folders synced to iCloud.)
I have a lot of Gmail labels. What's the best 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 options?
I use a lot of Gmail filters. Mail rules seem even better, but is there any way to automate transfering the filters to Mail?
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? 
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.
Tips for converting Gmail Contacts to Address Book.
If you've made the switch, I'd also be interested to hear your experience! I'd really like to get Mail up and running sooner and rid myself of Google.
Papa Bear

Answer 1

1: Smart folders won't sync between devices. But you can create regular mailbox folders under the icloud imap folder or at the icloud website which will stay synced.
2: The best way I see to do the labels is to create the gmail account in Mail. Set it to show those labels in imap in the labels setting section at the gmail website. All your gmail folders will appear under gmail's imap folder in Mail's sidebar. Then you will have options to export or just move the messages from one mailbox to another. I think I would just create a new mailbox under iCloud, then select all the messages from one gmail folder and right click to move the messages to the iCloud folder. Seems it would be the easiest way.
3: I don't think it is possible to transfer your rules from gmail to Mail. Rules should be very carefully constructed in Mail paying much consideration to the order they are placed. Simplify it as best you can and test it. In Mail, rules only will apply to incoming messages which may be different than what gmail does.
4: iCloud does not have the option to send other email addresses and retain their identity like gmail does. Best I can say on that is to create the accounts of the other addresses in Mail seperately with their own SMTP servers to send from.
5: No comment.
6:You can go to the gmail website and export your contacts.
Or, open up the AB on the computer and go to preferences. Open the Accounts tab. Select On My Mac in the list and check the box to sync Google contacts. Put your google sign in and password. Your Google contacts should be created on the computer. You can then select all the contacts in google and drag them to iCloud to add them. Once done, deselect the google contact syncing.