IPad – How to sync mail accounts between iMac and iPad2 properly

First - you'll want to set up two draft messages. One on the iPad and check using a gmail web interface if it's really storing the drafts properly to gmail. The iOS uses exchange active sync, but that shouldn't matter to you - either the iPad is storing it to the server (as viewed through mobile safari or any other web interface to gmail) or it isn't.

Repeat for Mail.app on the OS X. Here, you have more control (and more opportunity to set it up improperly).

The main item that would cause issues is if mail thinks it's not supposed to store drafts on the server. See the Accounts preference for your gmail account.

From there, you'll have to use the help menu to look into how to manually synchronize or run the connection doctor to see if/why mail isn't able to store drafts as directed. The last resort would be to hit up the google support link provided at the bottom of the mail account pane. Hopefully, you can suss it out with these tips.

Chase reports and asks:

Also, the folder ~/Library/Mail only has two folders

Mail Lost+Found V2 All of my mailboxes are contained within V2... is that normal?

Those folders should exist, but at least based on the contents of my own ~/Library/Mail folder, it's incomplete. I also have individual folders for each of my email accounts and those folders contain mbox files which I assume are the local copies of the IMAP mailstore.

By way of troubleshooting, it might be interesting to know what the file permissions are for the Mail directory.

Open the terminal, and type (or cut and paste) the following command:

ls -l ~/Library/Mail

The results (edited here to show only the relevant line) for my own functional Mail folder are:

drwx------    13 jaberg  staff    442 Oct 13 00:25 Mail

The permissions basically tell us that this a directory and that the owner, jaberg (me) is able to read, write and execute. (The execute permission of a directory is sometimes thought of as the search permission. You need the x in order to be allowed access to the information about the contents of the directory.)

You can also view permissions from Finder by selecting the folder and performing Get Info… from the file menu (or ⌘+i), but you won't get as much information.

You'll find more information about accessing and interpreting file permissions in the Apple Knowledgebase: Troubleshooting permissions issues in Mac OS X

If you're permissions differ from those shown here, you can try to Repair Permissions using Disk Utility (this doesn't require a restart or booting from a different volume) or, if you're comfortable, change the permissions of the Mail folder to match those shown using the chmod command. You can learn about chmod from its man(ual) pages, accessed from the terminal by typing:

man chmod