I am trying to make a switch from gmail to outlook but am facing many problems in that.

1) I want to send mails from gmail id itself. In other words, I want people to see that they received the message from that gmail id, though I send it from outlook. The same holds true with my school email id, people should see that the mail has come from my school email id.
I have set up autoforwarding in both the accounts, so I can receive mails from them. But if I send mails, my outlook email id comes in the "from" address, something which I want to change.
PS-My gmail id had a easy option to switch email accounts while sending emails.
PPS-I have added my gmail account in "Reply to-address" but it doesnt help.

2) Importing old mails from gmail. I dont know why you decided to leave your "trueswitch" application but now how do i move all my previous mails to my outlook mailbox.