Before you worry about the when and how, you should take a step back and be clear on your launch time goal.
With your initial launch, you don't necessarily want a big PR hit that draws 1000s of users to checkout your site. What you do want is a small group that joins your site and gives you feedback. Go for the big PR hit when you are more sure from your small user-base that you have a great product.
That was our plan. Fortunately(or unfortunately) we posted on the techcrunch forums and some people loved it and passed it to digg and soon it made the TC homepage without even submitting to them--making to TC was our 3 month goal.
With your initial launch, you don't necessarily want a big PR hit that draws 1000s of users to checkout your site. What you do want is a small group that joins your site and gives you feedback. Go for the big PR hit when you are more sure from your small user-base that you have a great product.
That was our plan. Fortunately(or unfortunately) we posted on the techcrunch forums and some people loved it and passed it to digg and soon it made the TC homepage without even submitting to them--making to TC was our 3 month goal.