Definitely cool. I was impressed when I found my Android phone doing this. I think it's useful and not just some whiz-bang feature. I think your argument for creepy is because you haven't used the Apple maps and may see it as a privacy concern since you didn't approve it to do this tracking. That was probably in your OS agreement. If you want to turn it off, there are instructions here.
My reason for feeling a bit creeped out is because it is tracking my location in the background without me knowing about it. Granted, I should've known and I should've looked back through every single setting when I updated. Mainly I just chose not to think about it until I was confronted with it front and center. I also wonder what other features are tracking different things without me knowing about it.
I actively tried to get the 'Google Now' app/thing to work for me to help my scheduling but it wouldn't. There is a bus stop a short walk from my place and I wanted it to let me know when it would come on a given day (it does seem to know the public transit schedule). It's been an exercise in frustration more than anything, because I know that it knows a lot about me but it refuses to assist me in anything other than its own time or way. For instance I will be walking around and it will tell me when the next buses are coming for nearby stops, except for the one that I live by. It has also guessed where I 'work' (go to school, whatever, I can forgive that) and what times I'm usually there, so it will tell me when I need to leave and what route to take at any time except when I actually need to leave, i.e. in the morning. I wouldn't necessarily mind having a system that notices my patterns and notifies my of when I need to leave, what route, what the traffic is like, etc if it would actually work and not annoying the hell out of me. And I'll be damned if I can ever get voice recognition to work.