I know for sure that your friend is allowed to book two rooms in their name, but I would imagine that some hotels would let it slide as long as you checked in together - or if they're sticklers, would at least be willing to change the second room to the eligible person. I might actually try doing it the other way around, booking both in the healthcare worker's name - then asking at check-in to switch it to your name and WoH account. Be polite, play dumb - fortunately, the terms are clear that each worker is 'entitled' to two rooms, so the worst case scenario is your friend earning the points instead of you.