a couple is always = 2 (from 2 people). generally a couple of [things] = 2 [things] ex) a couple of "days" = 2 "days", a couple of "months" = 2 "months" so yes, a couple of "hundred dollars" = 2 "hundred dollars" a few, means more than 2 ex) do you have a few dollars you can loan me? (more than 2 dollars) do you have a couple of dollars you can loan me (2 dollars) A.

In my opinion, 'a couple' is usually 2, not some. If you say 'a couple of hundred dollars', you would normally expect it to be 200 dollars, or very close to that amount. In this context, if it was some other approximate number, you would use 'a few' instead: 'a few hundred dollars'

As far as I can tell a couple isnt meant literally in this case. a couple = some Could be 200 or 600.. Another hundred dollars is always +100

so if a couple hundred dollars=$200, then does two couple hundred dollars=$400? Using the same logic applied, would three couple hundred dollars=$600; and so forth?

I really thought that I found a "false friend" here. Thats a word that seems to mean the same thing as in your own language... but in fact it doesnt. Luckily I looked a little bit around to verify this. It seems that a couple can mean various things like I first thought. The situation where couple=some seems to apply only in informal situations though. http://www.thefreedictionary.com/couple Thinking back I might have heard it in some kind of hollywood movie in a gangster setting. That could explain why this usage seems to be uncommon in the UK and Australia.