take the bar cover off and run the saw with the bar and chain off of it. Oil should be flowing at a steady drip from the oil line spout. If it is puking out the bottom, you may have to remove the clutch and check out the pump. it may be as simple as the pump is loose and not sealing against the housing.
This carb has limiters on them. All of the newer ones do to, becuase of the great EPA. If it is loading up, sounds like the carb is too rich on the low jet. You may have to remove the limiters to get the correct adjustment. You can have any dealer remove the limiters, or you can clip them off so you can get the adjustment you need.
Hope this helps some. Hard to tell what the oil problem is for sure. It may need a new oil hose between the tank and the oiler, if it is an older model.