I agree that VMs are a given.

I stick to Microsoft software all the way. Now my desktop/laptop client can be a client OS as opposed to a server OS due to the removal of technical restrictions from Win 8 Pro onwards. I would recommend forming a backup strategy to incorporate both to enable current work and to return to former work. Even if it is as simple as file copies.

As for licensing, I have an MSDN subscription (it was called Ultimate at the time i.e. the whole monty) which I have found to be rare amongst contractors, however, I have immediate access to pretty much all Microsoft software and I believe that most, if not all, are available within that licence for development. There are restrictions on the number of times you can install some software but with reasonably careful management I have yet to run out. I am sure that if I did run out then a call to MSDN would resolve the situation as they have the history of my licence claims to see that I am only using it appropriately.