Weird issue: Micro won't transmit win8

After lots of trial and error, I think I found the problem.

For some reason, my micro does NOT wait for a serial connection to be established before running the code including serial out.

Even sketches with the code to NOT send serial code until the serial connection is open, doesn't wait. If I do it as fast as humanly possible, I can sometimes get the end of it, like a few lines.

If I make the sketch continuously output the serial information (not once) and open the window, I catch it at the end before it repeats.

For some reason, it doesn't wait. I'm not sure exactly what would cause that. I'm running Windows 8 64 bit. I've used the Arduino 1.0.2 as well as the ERW-enhanced IDE. Tried several serial ports as well.

Is there a possibility my micro has a glitched bootloader or something?

I have a Mega 2560 r3 incase I have to do it.

This is really bugging me, I'm trying to finish my girlfriend's Christmas present.

I'm making a MAME/Emulator controller, with a built-in USB hub.

Currently this is how it is:
USB hub with external mounted USB-B connector (figure it would be the strongest: using a trimmed down panel mount usb-B to micro adaptor soldered straight to the USB hub
Micro going to buttons / analog sticks / added a button to switch between gamepad sending keypresses - accelerometer mouse control - analog stick mouse control - usb hub wiring
16gb usb flash disk. For space savings, I'm using a low profile micro-sd to usb adaptor, soldered directly to usb hub. using a class 10 micro-sd. may upgrade to 32gb as I have one laying around.

I'm still playing with different housings. I've completed a SNES controller as well as a PS2 controller. I'm just having issues debugging the code, so I went back to square 1.

Most of the code was done on the Mega, and I bought the Micro since I didn't need that many pins, and needed a small controller to fit within the size constraints.

I just don't know why the Micro won't wait for the serial connection before moving on...