Will that OS install go smoothly like with Boot Camp? Or will I run into problems. Or is it even possible on apply MB...
What OS? You said 2008 is running perfectly, so what OS are you talking about? apply mb? Do you mean Apple motherboard?
So, do you want to get and SSD and you are asking if installing the MacOS and the Windows 2008 server on the SSD is possible? Of course it is, an SSD is a Hard Drive. Use a cloning software to clone your current drive to an SSD if everything is currently working on it, or reinstall, it's a hard drive.
Next time, try to ask your question and explain what you are doing and maybe you'll get a better answer since you threw in things like the Wii emu that didn't have anything to do with the question, type in apply mb instead of Apple motherboard and you really never said exactly what you want to do.