A041 bars oil through the upper adjuster hole. There is no separate oil hole. The adjuster hole is open to the bar rail and this is how oil gets through. Same bars as my Dolmar PS340 uses. It is common for crud to clog up this passage in the bar rail so make sure to clean it well. From your 1st pic it looks like it is possibly blocked.
When you put the bar on the saw check the upper adjuster hole lines up with the oil groove on the saw. If it does it will be the correct bar and should oil if all other things are in working order.
Also make sure the area on the metal plate around the oiler hole and on the bar is nice and clean so it can get a proper seal and not leak bar oil. Same for the inside of the clutch cover that will sit against the bar and oil hole. If it doesn't seal off the other side of the oil/adjuster hole properly oil will go everywhere and not go to the bar.
Your pump worm gear is worn though. It should be flat all the way across and not worn in the middle like yours is. Fix all these things and i think you will be in business again