I noticed a few oil spots in my drive way, So i jacked it up and looked under and noticed the oil is coming from where the trans and motor meet, Almost looks like there is gasket there. It dose have 185k on it all stock, This past weekend i pulled a trailer for 400 miles then i started noticing oil. Think its time for a trans freashen up?

 

Is it oil or transmission fluid? If it is oil it is probably the rear main seal on the motor.

 

Its oil forsure, If its the rear main seal should i bring it to a engine guy or A transmission guy?

 

I would say an engine guy. The work to be done is on the engine and they can remove the transmission.