2001 Dodge Dakota (V8) forgot the engine size (its dads truck)

I have a bad shudder problem when i start out in first gear. the truck shakes bad. I know its drive line and aft of the clutch. its not a motor vibe problem.

A little back ground on the problem. Before i went on a trip pulling a 30' boat and a jetski in the bed of the truck i replaced the clutch, then on the way back i had another trailer behind the boat pulling yet another jetski. needless to say the truck was a bit weighed down. when i got home i found that i had cracked the out put housing on the back of the T case. we replaced the case half. and it worked ok. now this problem. so im just looking for ideas on things to check and look at. the only thing i can come up with is the pinion bearing. I think the heavy tq load may have done more damage then I thought.

Here is the pic of what i hauled