$200 each way = $400 actually. Also, my fiance lives down there and from the stories he's told me between him and his friends I'd be lucky to get it within 2 weeks b/c everything moves so slowly down there (yes, even things like Fed Ex and UPS). Also I have to pay the tax on that as well. So shipping it may not even be a great option.

I took matters into my own hands and talked to a Delta representative who took the time to look at the make of the plane I will be flying on and said I will have no problems with my carry-on. Especially considering it still fits within the 45 linear inches rule.
I won't be spending $140 on an ilugger either, but I wanted to use that as a reference.
So I managed to answer my own question.