Re: 2 Questions
Assuming it is the Chrysler mentioned at the bottom of your post, YES the upper bearing is lubricated by the lower unit oil. This is why it is so important when refilling to let the unit stand upright for about 1/2 hour to let air rise, then top off the oil. If the oil level is too low, the upper bearing will starve.
The distributor cap is two pieces. the top is held on by two screws near the center wire. Once you remove them, you pull off the top. The wires are pressed through a thick rubber seal and will come off the posts in the cap bottom. Pull them out through the rubber. Use Stranded wire, not automotive resistor wires. Do not strip the ends. Press the wires through the rubber enough so that they will be pushed tightly onto the posts when you assemble the cap. There are six posts in the cap (8 in the four cylinder). Be certain to use the correct three posts. The three with copper or brass flashing running down the inside of the cap are the incorrect ones as they are grounded to the distributor body by the copper.
Before you remove the cap, mark the posts 1,2,3. Firing order is 123 and If I remember correctly the wire closest to the block is 1 and the wire furthest forward is 2
It is not a difficult job but you do need to think about what you are doing.