Agreed, however there are a ton of companies with extremely outdated os/browser policies, that refuse to update for whatever reason. Been a contract developer for ~10 years and even this year we were told to support IE 8 on a specific project because some fortune 50 company needs us to (Seriously). There were plenty of modern tools that helped reduce issues but there was still a bit of headache.
Nope. There's usually plenty of work to do; supporting IE4 (or FF 3, or whatever Webkit shipped on Android 1.6) just makes it longer and over the budget, while squeezing out other projects.