Wait, what? Pay Cloudflare $20 a month to avoid a $100/year SSL certificate?

In their defense, you're also getting all the other features that cloudflare offers.

Keep in mind that you have to pay $20 / month to get host name SSL on Heroku even with your own cert, so from that standpoint this is a "good deal". However, one problem I've noticed with this approach is that in the cert Cloudflare uses you can see the 10 or do other domains that share the cert. I'm sure the average customer won't check, but having my cert also be valid for "cheaptoys.com" just felt wrong. Also, doesn't this mean the data is being unencrypted by CF then rencrypted and sent to Heroku? So CF can potentially see the contents of the transmission?

Yes, this allows CloudFlare to man-in-the-middle your SSL connection. Of course, that's exactly what it's designed to do.

This isn't cheap, it is easy though. SSL certs now days can be found for free from StartSSL and for around 10 bucks a year on places like Namecheap.

20$ a month is not cheap for SSL

I'm not sure whether I'm missing something but how can Cloudflare get a certificate issued with my domain?

What stops them from getting a cert for google.com or paypal.com?

I believe it's because cloudflare also acts as the root DNS for the domain, so in order for it to work for google and facebook, they would have to deliberately point their nameservers at cloudflare's DNS.

I should clarify - it's cheaper than a wildcard cert. It also makes it really easy for us to get private label resellers up and running.

This is also interesting for sites which can't acquire their own certificates (i.e., anything at .cu, .ir, .kp, .sd, and .sy).