I am an IT technician (business owner) by trade and have been for about 20 years. I see all manner of viruses every week, some more obnoxious than others. I've tried to infect machines and can't manage to get them as messed up as some folks can do. Not even sure what they do to get them that bad.
Security Essentials/Windows Defender on Win8 is fine for someone who is savvy and careful, but it IS baseline protection. The av-comparatives.org site IS quite useful at showing what the protection levels are. MSE comes in at around 80% protection. We generally recommend ESET NOD since it has a good catch rating, has a pretty low footprint, and has a good server based console for monitoring our business office clients.
Having a virtual machine is a good idea for web surfing. I don't do it personally, but if you have the extra hardware to handle a virtual machine, it definitely keeps your web browsing in a walled garden-like atmosphere.
Because I spend most of my time on my home machine doing all sorts of things and a relatively small amount on actually using it as a DAW, it's connected all the time. I use it for web development, which by nature of the things I have to work on requires it to be always connected. I don't have the extra funds to have a dedicated system nor do I have the overhead on the system to have a VM for web browsing/email/etc.
I just consider myself quite fortunate that I've only ever had one infection - gotten by searching for a recipe for baked shrimp scampi!
Bottom line: shellfish are more dangerous than Microsoft.
Hope this helps.