As far as I understand, the problem with IIS 7.x is that you can't set the host header for the SSL binding.
Using the appcmd command line utility you should be able to do this. The sites can use the same certificate but will have different host headers.
If you run the following 2 commands with your data, it should configure the host headers.
c:\Windows\System32\inetsrv>appcmd set site /site.name:"local.yourdomain.com" /+bindings.[protocol='https',bindingInformation='*:443:local.yourdomain.com']
c:\Windows\System32\inetsrv>appcmd set site /site.name:"local.dev.yourdomain.com" /+bindings.[protocol='https',bindingInformation='*:443:local.dev.yourdomain.com']
Unfortunately, there is something else you need to do to get this to work, but I'm not sure exactly what. I know I did some IIS resets, and I re-selected the SSL certs, but I'm not sure of the order in which to do that. But I know that I didn't do anything 'fancy' like use another tool.