Has anyone experienced a leak like this? (Very inexperienced yet broke driver)
 

I've taken my Chevy HHR 2008 LT to a mechanic several times over the last year for various issues, one of the more recent ones a few months ago to get the transmission fluid changed. Could this leaking brown fluid be related to that? It seems to be covering a large area but drips steadily, with maybe a baseball size spot under the car after a night.

TLDR: Anyone have a guess on what this could be?
https://cimg6.ibsrv.net/gimg/www.che...a67c353522.jpg
I jacked up the car under the front right tire to see what was going on, and the liquid moved along this piece of metal and is dripping at the circle now.
https://cimg7.ibsrv.net/gimg/www.che...f54d5d5bf9.jpg
This was what the liquid looked like.
https://cimg3.ibsrv.net/gimg/www.che...05670ebbbe.jpg
The drip was originally here.
https://cimg3.ibsrv.net/gimg/www.che...7e1a6b7ba6.jpg
Starter motor covered in oil(?)

Looks like a combination of sloppy oil filter change, oil pressure sender leaking and gravity.

I hope that you check the oil level regularly. Did this start after an oil change? Looks a bit like the oil drain is leaking.

Front main seal. Look at the mess on the side of the oil pan.

Could additionally be what Oldblue said.

Front main, or Harmonic balancer seal was my next choice! The starter covered in oil was why I suggested oil pressure sensor.