Traditionally when setting up SSL for an IIS website, you could generate a CSR using IIS to provide to your relevant certificate authority.
If setting up a website using the Azure App Service, the approach is slightly different. There's a myriad of ways of can do this, however this is the easiest approach I've found.
One of the most common Azure administration tasks is scheduling an auto stop & start of your Azure VM's to save you a few $$$.
Here's a quick post showing how you can do this.
UPDATE: Azure now provides the ability to auto start and shutdown ARM based VM's. If you are however still using a Classic VM, you can follow the below guide.