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I'm pretty sure I've found out what the issue was. A quick explanation of my initial thoughts first: I'm currently on vacation at my mom's and tried the Hero Lab demo on the local computer. This is however not my main computer. Thus, I decided I'd use the secondary license here, and activate the main license once back home. It might have been silly on my part considering there's apparently no difference between a main and secondary license (at least not in terms of rights and access), but eh, I wanted to be cautious.
Based on this decision, what I did was buy a license, and then immediately request the free secondary license and tried activating the secondary one. This never worked, with the previously mentioned error messages.
Yesterday I got a bit fed up and became more and more convinced the issue was that I was using the secondary license. I tried activating the main one and bam! it worked instantly.
Since I have a background in programming, I'll make a wild guess: my procedure is quirky enough that your servers aren't meant to deal with such a case and, when trying to activate the secondary license first, it fails on retrieving the game system chosen for the main license (a choice that hadn't yet been made in my case)... Thus, somehow, an infinite loop or something leading to a timeout of the process, whether using Hero Lab or the website.
If that's what it is, it would be nice to make it clear that secondary licenses are utterly dependant on the main ones, and if possible have an appropriate error message.
Now all I hope is that the secondary license will properly activate on my computer back home next week. I will let you know if there are any further issues.
Aside from this, I've finally been able to fiddle with the program and am an otherwise happy customer.
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