in reverse order:
- google talk is fine. I like digsby since it works with multiple accounts (of different types since I have aim, yahoo, msn, gtalk, etc) as well as twitter and facebook
- outlook is ok as long as you keep it updated. Outlook Express (the one that comes with windows) is full of bugs and holes. Just don't click emails that are spam. Get off yahoo and hotmail email and use gmail or gmail for your domain since their spam/virus protection >>>> MSN/Yahoo.
- Not sure what to tell you. If he's using IE he is going to get infected. Force the issue. Perhaps install firefox (shudder) and make it look like IE (http://geekace.com/how-to-make-firef...xplorer-8.html)