Once you get squared away with a Soundboard, the next step will be making sure the sounds you trigger are passed on into your Skype audio. This may require looking through the settings of Skype or the soundboard software. Don't worry - you'll eventually get this figured out.
I had thought that the speakers on my computer would be heard on the microphone on my lapel, but I guess anytime you go through the air you are losing something as well as adding background noise. It will clearly take some experimenting. I have tech people who although are not sound technicians might be able to give me a better idea.