I figured I'd share my experience here!
I'm glad I changed the oil! Mostly for peace of mind to know when it was done last and when it has to be done again. Didn't take much time at all. Here is a comparison btwn the old and new oil!!!:
The syringe I picked up worked great to fill the reservoir, its made by Chefmate, its a "flavor injector," got it for $3 at my local target store. Highly recommended for filling the system! I had to use a smaller syringe to draw the fluid out.
How often should I change the oil in the machine?