8 oz of chain-case oil is correct. This should show the oil level ~ in the middle of the double headed arrow on the STD side of the stick. Forget about the REVERSE side of the stick. There is a vent in the rubber on the stick. No pressure will build.
The bearings to pre-oil are the needle bearings. You are correct.
You are putting in a new unsealed bearing this time. Is that correct?
When you assemble it this time, I would leave the chain off and put on the cover and rotor, etc. If the jack shaft turns freely by hand then remove the cover and install the chain. You may want to tension the chain with the cover off to see how well it fits, how much adjustment you have left, etc. You do not want to spin it using the motor until later, when you have added the oil.
When you adjust the chain tension for the last time, I would tighten it finger tight and back it off ¼ turn. The reverse works better with some play in the chain and you will take unnecessary pressure off the bearings. The chain being too tight could have caused your first replacement bearing to fail sooner than expected.
Is this your very first chain? If this is the chain that went through all these problems, it is possible that it could be adding to vibrations causing pre-mature bearing failure. However, if there is a lot of adjustment left, I doubt it. But, I would lay the chain in both of the gears to see if the chain fits snuggly on the gears. I think you will be O.K. But it is one more thing to rule out.
I would be interested to know about the TIR after you take the jack-shaft into the shop. Given the measurements you have already taken, I think you will be O.K. But, it is one more thing to finally rule out as a potential problem.
Once you have it all back together and have the oil in it, then it is time to try it with the Engine. Again, I would be keeping a hand on the cover to see if it gets excessively hot. Watch out for the rotor. It will bite you, if you get too close. I would rev it a little and stop the track. Then put on the ol' paddy. Rev the thing up a little more. If it stays cool or uniformly warm as the rest of the cover, then take her for a spin. But, keep occasionally testing it with your hand for a while.
Use the exploded view drawings to verify every part is being installed correctly. Sometime I still have to go back to it. You can even use the ZOOM feature to blow the parts up in size to figure out the correct orientation. If you zoom in you can begin to see the discrete differences in one side or the other of some the parts, etc.
Watch that cover gasket. Often, the simple things get us. Make sure it stays put. Check the oil level frequently for the first 10-20 miles. Then after 50 miles, drain it through a rag and look for metal. Replace the oil and you should be good to go for a while.
Good luck!