One note here, if you're using Google Apps, moving should be a breeze as you can just change your MX records. However, hosting your own email could be painful.
For me it is especially great since my primary email is an alias domain on Google Apps, which means i can move my primary email off of google apps while keeping my google account working (also grandfathered into their free plan).
So switching email is just the matter of picking my own host. That could take a while, however.
>hosting your own email could be painful //
In case anyone missed them and is interested a thread on HN recently gave some recipes and outlines for setting up email servers.
https://news.ycombinator.com/item?id=6748670
There are a few in the thread besides the OP.
For 3: email forwarding + vacation autoresponse help a lot. You get the messages anyway and whoever emails you gets an automatic reply with your new contact information.
I posted below that FastMail is a good Gmail alternative, and switching isn't that painful. See http://www.maxmasnick.com/2013/07/19/fastmail/
(Posting again here so you (might) be notified.)
For basic video chat, I recommend Talky which uses WebRTC to implement group chat, including private rooms and screensharing:
2) I've also switched to DDG, but I still find that google gives me somewhat better results for things related to programming are academics. Apart from that, I like DDG a lot.
3) That's the big, big problem for me. I could stop using virtually any other product labelled google without problem (ok, youtube excluded), but gmail keeps me there. Not so much that gmail itself is so great (it is good, for sure), but the act of switching emails, updating contacts left and right, is just a pain.
4) it seems to me that most providers for hangout/video type of things are equally obnoxious with the way they handle your data..
Going back to the email stuff, I guess I'm also waiting for a decent alternative to pop up, as I'm not inclined to switch 10 times in the next 6 months..