Crank the oiler up to the max. The oil tank is supposed to have oil left when the fuel runs out. It has more oil then fuel so the oil doesn't run out while you are using it. Looks like thats where you sre doing the most cutting on the bar. Make sure you flip the bar every now and then to spread the wear out more evenly. If you cut in the same spot on the bar it will wear the most in those spots. Try to use different spots on the bar to equalize bar wear. But it looks normal to me.
As for the groove getting saw dust and preventing the oil from getting to all parts of the chain and bar is not a big deal. That saw dust gets soaked in oil and the chain will drag the oil to all parts of the bar no mater if it is clogged with saw dust. I only clean out the bar groove when I change the chain or flip the bar. I typically only flip the bar and clean the groove when I put on a new chain.
However, if you hit the dirt, please stop and clean the bar groove because the dirt will grind and wear things out faster. But just saw dust, not so much.