there are certainly no wrong moves when decided what operating system to use for anything. Although both have there pros and cons, it really comes down to choice of preference.
Macs are awesome for production, and are consider the industry standard operating system for editing/producing anything. weather it be audio, film or pictures, editing is easier, quicker. These computers are build for this kind of work. but, like you have already witness, updating can be a pain as technology advances faster each year. i'd suggest staying with mac if you "can" afford updating your computer every 2 to 3 years. Another great thing is that Macs are well protected from virus, which leaves all your work, risk free :)
Windows on the other hand, is great for customizing and updating your operating system frequently. it is also very affordable for the average musician/producer. if you do decide to go back to windows, i highly recommend to not use the internet at all. It can put your computer, and anything on it at risk from virus infection. Other wise i don't see a problem with using windows, it can do anything a mac can but was built for mainly business use.
In the end, it is probably suggest you go with whatever is more affordable. Both are capable of great things, one is just easier to edit on (Mac).
If i had the money for updating, i would go with Mac.