WOOHOO, OH YEAH I FINALLY FOUND A WAY!

Problem was Winsock didn't reconize Collection data type so refused to send, so what I did was modified my DirList function to return a PropertyBag and then turned it into a byte array before sending it.

Here is a link of a good thread that shows a few example codes that you can use to achieve exactly that.

http://vbforums.com/showthread.php?s=&threadid=242564

Thank you to everyone who was in that thread I linked, that was a good example I needed to figure out my problem. Took forever to dig it up too.