I convinced my PM that I needed the debugger for my recent project. I have not really used it much however, as I ended up doing so much front end work.
Also, with lots of unit tests, you don't need it as much either.
One thing that was very annoying was that any time metadata on the project gets saved, your session gets killed. Which was a lot.
However, in general, the debugger works very well.
- It is pretty fast (maybe 1-2 seconds to stop at a break point)
- It works for triggers
- It works on Page controllers - ie, you visit the page with the break point enabled, and it catches it no probs.
- It even works for Apex lightning controllers ( I am using an embedded lightning lookup component that I built in my VisualForce page )
Here is the evidence:

Caveats:
It does not work currently with Eclipse 4.5 (for me anyway). The entire Force.com environment failed to load.
Also make sure you follow the process described here. I had a lot of trouble with the debugger until I followed this process exactly (I initially just made a Force.com debug configuration and started a session without setting up the perspective first as described in the above webpage - it failed to stop at any of my break points)
And finally, yeah, I think it's costing over 1200 a month, which given how much I've used it is probably not worth it, unfortunately. However, given a different project and different mix of coding tasks, it could be extremely useful.