This series of articles from PC Magazine has a ton of good ideas, tools, tips, and whatnot for getting started and thriving in a telecommuting arrangement. The tools are probably not going to be news to most of the hard-core remote working enthusiasts out there, and frankly they've picked the most blogged about stuff out there. You might do better to look at sites that do nothing but worry about webworker tools.
But tips for convincing your boss to let you strap on slippers -- you can never have too many of those! I absolutely love the idea of taking bullets for the team. This is a great idea, and it goes beyond taking travel gigs that everyone else is dreading. I will always try to volunteer for late-night upgrade babysitting duties, staying late to take a vendor call during a technical issue resolution process, dealing with after hours support calls from customers, or checking critical systems on a holiday. It's not like I have to go extremely out of my way to do so -- I just stumble across the dang patio. Easy as pie.
Look, dear readers, you have to be honest with yourself: telecommuting is an enormous and pleasant luxury. Not everyone gets to do it, and you're really lucky. You have to go the extra mile, and picking up those rubber chickens when you can is a a good way to get started on that extra mile.