What are the reasons to jailbreak now? You get the apps for free, you can tether 3G to your laptop/iPad right? Anything else new that's happened in the last couple years?
Most people I know don't jailbreak for free apps. And, by default, those aren't available - you have to go hunt for those repositories.
I have jailbroken my old iPod Touch and my iPhone 3GS for the extra functionality and flexibility. Apps that Apple rejected for silly reasons - those are in the default repo. Apps that bring functionality which may or may not eventually show up in iOS. For example, quick app switching was available on jailbroken devices before it was added to iOS.
Apps like SBSettings give you customizable one-touch access to toggle all your radios, your brightness, most anything. Activator gives you the ability to customize how you switch apps, go to the home screen, etc. I find it faster and simpler to just swipe the taskbar to go "home" rather than hit the home button (and, on my iPod Touch with its broken home button - it lets me continue to use the device!). Being able to customize your lockscreen is a big one for a lot of people.
In short: It's mainly about adding functionality, not about thievery.