Yes, reserve to upgrade for the same reasons Tom said.

I'd also go as far as actually updating it. You are familiar with windows 7 and Windows 10 UI paradigm is closer to that than 8 is.

The benefit is that you have the latest features and updates, and I'd say, generally, the sooner the better.

I've been using the various previous since the beginning, and overall I really like it. I did like 8 too, so if you did not, take my opinion carefully.

Also, now that you have a VM ready, you'll be able to simply migrate that to the new OS install and that won't change a bit.