If you're even close to going forward with this, definitely lawyer up. Especially considering you're talking about a "loophole". Also talk with an accountant wh

If you're even close to going forward with this, definitely lawyer up. Especially considering you're talking about a "loophole". Also talk with an accountant who has helped people in this situation, as that can cause some big surprises when it comes to what you owe at tax time. Consider where you're leaving behind: KW is a rad area; I've been here in the startup world for just over 3 years (born and raised not too far away). A decent starting offer here is $60-80k, potentially more if you're at a 'name brand' company (I started at $65k for reference, with $50k the number I had in mind to stay local after wrapping up my CS degree). The cost of living here is way less than SF, so there's lots left over for actually spending on living. If you really want to be in a city, go an hour east to Toronto and make your mark there. I know the valley is a mystical, magical place, but if you're putting salary/equity high up on your list of "Pros", consider that you could do just as well, or better, in the area (when looking at purchasing power, cost of living, etc).