We've successfully upgraded Windows 2008 R2 to Windows Server 2012 R2 and then up to Server 2016 with MS SQL services installed, and had no issues.
Anyone who works with SQL will no that its a pain in the ass on a good day so an upgrade without any issues is a win.
Best suggestion is to convert your physical machine to a virtual, and then test - thats the only way you discover any issues.
Smartermail 15 will run fine on server 2012 R2 so theres no reason to be concerned about Smartermail - Just make sure that Mail services are stopped at the time of upgrade - I would also stop IIS.
Jade
https://absolutehosting.co.za