I don’t have to plan for it. For the last month I’ve been getting notifications to reserve my copy of Win/10. I think I will wait a couple of months before I bite. Hope they don’t sell out so I kick myself in the butt for not reserving. Oh well, living dangerously.
Nah, you'll be okay waiting. That's what I'm doing also, for the one of my Win7 machines that I plan to upgrade to Win10. The rest are staying with Win7 until 2020 when the Win7 security updates stop. By then there may be better options.
Anyway, Microsoft can't "sell out" -- it's just software, and they don't even have to make DVDs. Copies of software are pennies each to make, if that.
If you are willing to believe that they aren't lying about the "one year from date of release" for the free ugpgrade, then you should be able to wait 11 months plus a little nail-biting time.
They do say you’re not committed to the upgrade if you do reserve it.