I've got a lot of dark sports on the front of the engine due to a past oil leak. I've been considering painting it, but not sure if I should. What do you think?

And if I did paint it, is there any specific way to go about it?

 

Painting is always the cheap/incorrect route to go when it comes to something that should be powdercoated or ceramic coated. I saw some guy on here did a very neat masking job and painted his whole engine black. In the pics it looked good. Up close? - Who knows. Best advice I can give you since it will be almost impossible to sand or scuff the entire thing is to hit it with like 2 coats of etch primer so it can eat in and the paint (high temp) can bond well. Good luck.