I'd say it depends on the level of security your users would expect from your site. About the same level of security as posting on reddit or HN, which is why I

I'd say it depends on the level of security your users would expect from your site. About the same level of security as posting on reddit or HN, which is why I used them as examples. Submit this, vote for the best that, etc. A closer example might be StackOverflow, but I honestly have no idea what goes into logging in over there, since it's all done behind the scenes with OpenID (though there was nothing https-y shown in HTTPFox when I tried it). If there's financial data involved Nope. Monetization, initially, will be provided via affiliate links. If you buy something you saw on my site, you wouldn't be buying it from me. Also: an upgrade to your site is easier to sell your users ('now even more secure') than a downgrade. This is my thinking. If the site ever gets to the point where it's nicely paying for itself and I can justify the cost of the static IP and the cert, I will.