Jake,

I think the move to stay outside the US is a wise one. If you host inside the US then you give the Feds something they can seize. Of course, technically they could still do so in Canada, but it will never happen.

However... conveniently, NatNet has a data center in the Netherlands which serves all of their customers who want servers outside the US. I have to agree with Lee here, we have been with at least 8 different hosts in the US over the past 8 years, and I can tell you from experience there is simply nothing remotely approaching NatNet as far as the quality of the service and support you'll get. Particularly for a new webmaster, NatNet's team will allow you to do what you do best without messing with the backend crap that you'll have to deal with (in one way or another) with most every other host, even the ones that claim to be "managed." I never believed the hype about NatNet until I actually experienced their service.

As far as following 2257 to the letter... I would be willing to wager that 90% or greater of US-based affiliate programs don't follow it to the letter. It's exceptionally complex and 3/4 of the webmasters I speak to don't even understand all the nuances of it. (I don't claim I do either, just that I seem to know more than a lot of others.) So as long as you're making an honest good faith effort to comply, I don't think it will affect your ability to market to US-based affiliates. We've spent thousands of dollars on developing our own software for compliance, and probably thousands more in staff time inputting and cross-referencing the data, but we're also pretty conservative about compliance, and you can get away with a lot less, particularly since, at the beginning at least, you won't have a ton of content to mess with.

I will also give a strong endorsement for Strongbox. Ray Morris is an absolute topnotch guy, knows his shit inside and out, and has probably forgotten more about web security than most people will ever know. Cozyfrog is one of those companies that sells a lot of the sizzle rather than the steak, and their product might be fine, but honestly, there's a reason that Strongbox has a very large percentage of the market, and it's because it's a great product from a great guy who believes in providing excellent support and assistance, and not ripping you off on endless recurring monthly fees.