Solution 1

use GMAIL Mail fetcher to retrieve automatically all emails and tag them accordingly. All you have to do is to set up GMAIL fetcher to retrieve and tags your old email one step at a time. For example, I decide to migrate all my Joomla email away of Hotmail.

1. I empty or move all items of my hotmail inbox  in another folder,
2. I set GMAIL fetcher to retrieve and tag all my items automatically with a new tag Joomla (using “Label incoming message with”)
3. In hotmail, I move all my old email from the folder Joomla to the inbox,
4. After some seconds, all your email will be moved to GMAIL, and  the date and timestamp is preserved.
5. Do this for all your email one category at a time till your Hotmail inbox is empty.
6. Keep GMAIL Mail fetcher to retrieve automatically all future emails

The only issue is that emails from the junk folder are not sent to GMAIL. A visit to Hotmail is still mandatory every months or so.

Solution 2

Export all your email for archiving on disk with Windows Live Mail Desktop, then use GMAIL Mail fetcher to retrieve automatically all future emails

Get multiple e-mail accounts in one program – Hotmail, Gmail, Yahoo!* and more. And now Windows Live Mail has a calendar, too. Mail combines the ease of use of Outlook Express, with the speed of Windows Live.

Outlook won't let you connect officially, you need to pay! but Windows Live Mail Desktop allow you to connect to your free Hotmail accounts, and drag mail into IMAP mail accounts as well as "Local Folders".
it stores local copies of your mails in a folder (which you can configure using Tools -> Advanced Options), so you’ll end up with many directories containing *.eml files. Perfect for archiving your old emails.

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