First thing in the day, does your rig take some time to turn over and fire up? If so, then there's a real possibility you're losing your fuel pressure in the manifold. Leaking fuel injectors can do this for you. Might want to troubleshoot that direction.
Peabody, in your case, fix that hose and see what it does for you before tearing into it some more. Ya might be working this out in layers.
Fuel getting into your oil and diluting it is called 'washdown'. It ain't purty in the end. Carbed rigs' symptoms for startup are identical; culprit is the float needle lets the fuel out of the bowl.
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