All great suggestions. The bike had been ridden a bit over the past year, so it wasn't as if this was first startup after sitting for 10+ years. I'm trying to arrange pickup with him, we will see.

 

 

Should be picking her up today. Will report back once I figure out the source of the leak.

 

Sounds more like a stuck needle/seat or heavy float and oil out the breather. Also could have wet sumped. All the oil running out would be from the oil tank or the breather. The only way it would come out of the engine would be if it were completely wet sumped and there was a hole in the bottom of the case.

I'd recommend diagnosing before you buy an engine and assume it "blew up"

 

Max had a good suggestion in his post about the timing plug. Repeating my thoughts, you could have couple things going on and Max is suggesting similar things.

1) In a Softail all the oil is in the tank above the engine and gravity makes it bleed down into the engine through the check valve in the oil pump. Then when you turn the engine over, it overwhelms the return & breather system and comes pouring out the vent line under the bike. In an EVO, it will typically be a breather hose under the bike somewhere with a little filter on it - most likely near the rear under the frame.

2) If the carburetor is leaking past the needle and seat and the engine has filled with oil it also means the vacuum petcock has failed. That could be the fuel out the exhaust. If enough leaked fast enough, it can run into the intake, into the cylinders and leak past the rings into the bottom end.

Does the oil in the tank smell like fuel?

ALSO - Softails must be run prior to adding oil. When they sump through the pump, and people look in the tank and it's low, they actually overfill them. The oil must be returned to the tank prior to checking level.

 

Excellent feedback. So, I cranked it again today. Didn't start, and then oil rushed out a filter behind the jugs. I'll post pictures when I can get some. Pretty sure the oil smelled of gas.

Interestingly enough, the insurance names the bike as an "94 HD clone." The frame is a softail, not sure if factory harley. Most parts have HD emblems, however the motor says 80 inches, dyna wide glide.

What are the appropriate steps for fixing if that is the case? I'm going to pull the carburetor and clean it. New petcock? What else?

 

Just pulled the dipstick, does smell like gas

 

 

Once you validates that it runs OK, swap out the tires, bleed the brakes and make sure they work without hanging up and lube all the cables. I'd check all fasteners, even change fork oil.

 

Bike has manual petcock. Doesn't appear to be leaking. Ordering a carb rebuild kit, new plugs, and new air filter.