Just remember to not go too much, it just needs to be a smooth transition for the rings.
That's great to hear, it's their fault for not properly packaging their items.
Oil is a big deal on these old motor. Meaning using oil and proper amounts of it. The brand/type is subjective and up to much debate.
I recommend 16:1 for break in, 20:1-32:1 after on chrome cylinders 24:1-40:1 for sleeved.
As far as type and quality. Do research, check the ingredients using the material data safety sheet that a reputable oil company should have.
Personally I like castor based 2 stroke oil.