It is unwise to manually push voltage regulator or cutout contact points together manually, it is just asking to have the magic smoke leak out of the charging system!
Cutout points aren't supposed to close until the generator voltage exceeds the battery voltage, and it seems your generator is not charging adequately, so the cutout won't close.
Try this tomorrow, start the tractor back up, keep your itchy twitchy fingers out of the VR or cutout, and measure the voltage at the "A" (Armature) and "F" (Field) terminals with respect to chassis ground and post back.
(Someone will no doubt come along and suggest polarizing (which is a good idea) but you actually already did that when you mashed the contacts closed. You are just darned lucky they popped back open when you shut down the engine!)
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