2. There are many services that let you monitor the expiring domains and notify of changes. One I use is domaintools.com for about $15/month (they also have a bunch of other useful features). They send emails when the domain's status changes. But I think it's not hard to build a script that would do that.
Other good services:
other interesting sites to check on the matter:
read more info here
3. to backorder at godaddy, as mentioned before, use the godaddy backorder and bid on tdnam. If it's on other registrars place bids on pool, namejet and snapnames as well as you can't always know where it will end up.