Coming back to your first question:
"If you raise the moter to adjust the transfer case output angle, what happens with your front pinion angle .... especially if it needs adjustment and you are happy with your caster?"
Raising the motor has very little impact on the height of the transfer case's front output shaft which is set by the rear transmission mount (T-case drop). It simply rotates the T-case to point up slightly (and rear shaft points down slightly). The hight of the transfer has a large impact on drive shaft angle. The minimal change in hight means that there is minimal impact on the front drive shaft angle which should leave it aligned with the pinion angle (CV front drive shaft). Therefore there is no real impact on your front axle or caster. As Andy pointed out, the angle between the driveshaft and the transfer case is not important because the CV joint handles the angle.
However, in the rear, with a non-CV drive shaft, the relative angle between the T-case output shaft and the rear pinion is important. Therefore the motor-mount lift allows for the rear axle to be set at steeper angle. If your rear axle is already properly aligned, then adding the motor and adjusting the rear axle accordingly will raise the pinion and push the track bar closer to the gas tank (not further).
If you were to switch to the CV shaft, then you would need to rotate the rear pinion up even further to be in-line with the drive shaft, which would require you to rotate the axle back further and make the track bar situation worse. Because of the location of the transmission/T-Case mounting point relative to its rear output shaft, raising the motor mount will give you some decrease in absolute height of the rear T-case output shaft and therefore a slight rear drive shaft angle reduction and allow you to slightly rotate the diff back forward.
Generally speaking, increasing the motor mount height helps to compensate for rear pinion angles that are too high with non-CV rear drive shafts. Many of the lift kits provide longer lower control arms that are longer than stock and rotate the pinion down to alleviate this issue.