Why is it that on both shots, on a medium hit, I need to aim at the same location on the rail, to pocket the ball even if the contact point of the tip to the CB is on the upper RIGHT side and the other shot is on the lower LEFT part of the CB, is my aiming off? ...
If you have played for a while, your perception of the line and the actual line may be different. You could test for this by having a camera looking back towards you on the two shots.
If you really want to learn the theory, spend some time on Dr. Dave's website in the pertinent sections -- squirt, swerve, aiming. But briefly....
Squirt, swerve and throw all change which direction the stick needs to be pointed. Swerve and throw change with speed and spin. This makes aiming with side spin complicated. For your low with outside shot (lower image) for some speeds you need to aim fuller than for a spinless shot and for other speeds you need to aim thinner. That means for the right combinations of spin and speed you can aim as you would normally and have the cue stick parallel to the line for a spinless shot.
Using draw delays swerve and the ball curves over a long distance. On follow shots with side, the swerve takes place almost immediately. Draw with side usually has more total swerve because the stick is elevated more.
Contrary to what was said above, even follow shots have enough swerve to causes misses for long shots. The cue stick is elevated on nearly all shots -- no one plays with a level cue stick.
This is only a brief summary. The real bottom line is that you have to learn where to point your cue stick to pocket the object ball with all these effects going on. That is best learned through focused practice.
Here's a practice: in the shots above take the cue ball two rails to different targets -- just to the second rail, a diamond farther, a diamond farther, .... Repeat for each distance until you have gotten "close enough" three times in a row, then move to the next farther distance.