If you ever look in the rad fill cap you will see that the factory "cooler" is really nothing more than a single tube that connects the two trans line fittings. Personally I would skip the factory one in the rad (unless you drive in freezing temps and need it to warm up the trans fluid).
I would go a shift kit, auxiliary cooler and whatever rear gears you like (personally I had 3.73s). Don't need the stall converter unless you are needing higher rpm launches. The factory converter will work great for a cruiser. Most aftermarket cams suggest a higher stall converter so that you can maximize the power their cam can produce (most make more power higher in the rpm range and actually kill power down low - hence wanting you to rev up before you get moving).
I would go a shift kit, auxiliary cooler and whatever rear gears you like (personally I had 3.73s). Don't need the stall converter unless you are needing higher rpm launches. The factory converter will work great for a cruiser. Most aftermarket cams suggest a higher stall converter so that you can maximize the power their cam can produce (most make more power higher in the rpm range and actually kill power down low - hence wanting you to rev up before you get moving).