If you adjust more slack into your linkage, you will shift earlier and softer. BUT and I do mean BUT, you will potentially shorten your transmissions life. By reducing the throttle signal to the transmission, you reduce the line pressure, which reduces it's torque holding capacity. However, if the linkage is to "long" the transmission will think you are under a higher load and raise shift points and firmness accordingly. If the linkage is way to long, you will not get full throttle at the carb.
Here's the basic thing to look at with the linkage. The lever on the transmission should JUST touch it's rearmost stop when the carb JUST hits wide open throttle. So long as you are using some version of a Chrysler compatible carb and an unhacked OEM linkage, you should be fine. A factory service manual will have a great picture and instructions.
If you set it per the above and your transmission will not upshift, you have some other sort of problem, such as a screwed-up governor or a $40 shift kit.
No need for a jam nut, the linkage cant rotate once connected.