Ok first off big thanks to Ortega for helpping me work through this.
I am not sure what part exactly de bugged the quest but here is what I did.
Make sure you have over 20,000 credits when you start this (will need over 27,000 to finish whole chain)
1.Talk to Louden, get both quests.
2.Talk to louden again learn about Holly being crooked
3.Go kill ships
4.Go to earth pick up o2 canisters only not terran insigna.
5.Go back to Louden hand in kill quest
6.talk to louden again, should now be promtp for quest to give him 20k
7.talk to loden again, now he wants the terran insigna
8.Go to ES pick up terran insigna and L2 Orb weaver ML to save time
9.go back to louden hand in o2 and insigna quest
10.talk to louden again, now he should take your 20,000 credits
11.talk to louden again he will ask for orb weaver
12.talk to louden again hand orb weaver, get skill.