(about spoofcard) good, that's what spooftel does as well. I wonder if it's domestic. US companies are slightly more bound by US laws than canadian ones are, and with everyone being considered a terrorist for sneezing near an airplane, let alone hacking, I'd be careful about using a US company...
I very much doubt that you could get skype to do anything like this, as the software that chooses and assigns a phone number for you over skype is probably on their servers.