[VWNate1]

How many teeth are on the starter's Bendix ? .

Once in a while you'll get an odd tooth count and this causes jamming & binding .

Dano , you said oil droplets all over the back of the cab , that's not likely rings as rings woud spew oil & smoke out the exhaust pipe , not from under the cab....

I'm just thinking out loud here , maybe you blew a rear main seal or oil filter plate seal ? .