The oil cooler never gets warm, like there isn't any oil going through the lines. Did a full oil change with a new filter and blew out the lines to the cooler and everything seemed peachy. Slap it back together and the oil cooler still never gets warm...the lines don't even get warm. What gives?

 

Unless it has a clog or pinched oil line somewhere its pretty well a full proof simple thing a oil cooler. It just redirects the oil the long way around to give the oil time to cool down before re-entering the crank case.

If the oil pump was not working you would know by now. I never bothered to actually touch my oil cooler while its running, maybe they just don't get hot. I will try it out and get back to you.

I know it takes a heck of a lot of riding to get the oil cooler fan to kick on, I almost though the fan did not work.

 

I blew the oil coolers lines out with compressed air and it seemed to flow good so I dont think it is a clog. My cooling fan has never come on and I know the bike has gotten hot enough that it should have. That's the first time I realized that the cooler isnt even warm.

 

Don't worry to much about the fan. My 1989 350 Big bear is still running and it never even has a fan for its oil cooler. Its the same motor as your 386 but with a smaller 64mm stroke making it a 348.

You could disconnect the fitting #20 to see if oil is pumping out, cant hurt anything for a 30 second run. I,m not sure which one is the line that oil enters back to the motor though.
The pic show no fan for 95 are you sure the fan is stock?

 

Everything about the fan looks stock. For all i know it is a newer bike and an older title bc the guy was a bit shady i bought it from lol. Either way...cooler should be getting warm I think. Ill have to take that fitting off and see if it is pumping. There is no way it could be bypassing the cooler, right? I noticed the oil filter has a bypass...but the bypass route wasnt apparently clear to me...