It probably depends on which kind of license one starts with. Here I am on third almost complete machine (including motherboard) but all started from Retail W7 Ultimate and same hotmail.com account and it never refused to activate automatically. Had to confirm account few times and that was all.
My Windows 7 is OEM Home Premium and I've never had problems reactivating on that one, so maybe I'll be lucky with this Windows 10 that comes from it. I checked the activation and I have a digital license connected with my account, which makes me think everything will go as planned hopefully.
Thanks everyone, I can mark this one as solved for now since all questions have been answered and I won't be able to verify until I get to it in a few weeks :)
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