The time is running out for the free upgrade. What are the reasons one should do the upgrade and what are the reasons one should skip the upgrade?
In my specific case I run Windows 8 very rarely in VirtualBox, so I wonder about the license implications for that.
I do understand that there are lots of articles of different degrees of credibility all around the web, I would just like to see the collective wisdom of HN readers to produce somewhat balanced arguments for both sides to help doing the decision.
Having said that, the main reason for at least initiating the update is to mark your existing key as "Windows 10 eligible". After the upgrade is complete, you can easily roll back to the previous OS version (from within Windows, trivial and no side effects) and you can continue working on Windows 8.1 while now having a valid Windows 10 key for the future.
You can also perform the above procedure using a VM snapshot, upgrading, and then simply using your snapshot instead.
If you are a developer using Windows as your main OS, a very strong reason to upgrade and not roll back is the upcoming Anniversary Update. This will bring the "Windows Subsystem for Linux" which means you can natively run the entire Ubuntu userspace, like bash, tmux etc. That is pretty exiting!
IMO if you rarely use the VM in question, your top priority should be future-proofing your Windows 8 key.