My poor boy is scared of everything! Large bags of foliage, large men, umbrellas, basically anything that is large, over him and foreign. He doesn't even like umbrellas + children and starts to shake uncontrollably, and it's so sad to see. 


I was wondering if there's anything we can do to break him out of this?


Backstory: our former room-mate thought it would be FUNNY to tie balloons to him, knowing he was scared to death of balloons. Zwei ran around and scared himself so much that he was literally having PTSD after the fact (looking up all the time, looking for balloons, scared to go outside). He's gotten better since then but ... :(

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It sounds like poor Zwei has been pretty badly traumatized.  You should get some help from an animal behaviorist to help Zwei get past his fears.   It may take quite long time in a step by step process for him to get his confidence back.  If you don't address his situation he could turn to fear biting and then you have a much worse situation. 

As for your former roommate, I think he should be tied up in the park so people can torment him and he can see what it's like.  %^%$# !!


ditto-to the former room mate!  Look into Obedience and/or Agility classes. That can really improve their confidence. Mean while start very slow exposing him to things. For example: treats if he can be 20 feet from something he is afraid of etc.


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