[viC]

With a decent degree and a year or two of work experience immigration to Canada/Australia is pretty simple [I only know about Canada but it takes some time to get your application approved and such.]

I think there are a couple of issues you should consider here though:

1] Why the fixation on an English-speaking society? Consider working for a multinational where all your work is done in English but in a non-English-speaking country [China/East Asia, Europe, South America] You're 23 so you don't exactly have to pick a city to settle in and never leave, and traveling around soaking up different cultures can be very rewarding at this age. There are also a number of multinationals that would rotate you to a different country every year or so, but I'm not sure about IT roles doing that.

2] If what's limiting you from getting your East Coast Dreamlocation/job is the fact that you're "the most average ITer" out there, then simply broaden your horizons by ditching that label. Think long term: if switching jobs to something more specialized where you are now means you can apply to specialized positions in the states in a year or so, then it is probably worth it.

3] The Green Card Lottery is exactly that, a lottery - don't hang your hopes on winning it. Unfortunately the situation in the US isn't much better when it comes to company-sponsored IT work visas [H1B visas]. They're extremely limited in number, and tend to get snatched up on the very first day by large outsourcing companies. You would need to apply well in advance [they're given out in May i believe so applying by March at the absolute latest is recommended], through a company that can put your application through, and then cross your fingers.