I am specifically wondering if this question should or should not be allowed? I never heard back from any mods on this one. If it is off-topic is there anywhere on the stack exchange network where it would not be considered off topic?
I reopened it before seeing that there was an ongoing meta discussion, so here's my rationale:
The question in its current form seems to be specific enough (after being edited) that I wouldn't have closed it in the first place.
Licenses, especially in cases involving Microsoft, often seem to change a product in many (sometimes confusing) ways. In this case, there are at least four basic options (PDF download), and there seem to be additional convolutions based on the number of cores, etc. that you need to support. I could make an argument that they're actually different products.
Based on the complexity of the choice, I believe that, at least in this case, the question is a good fit and is something we can help with. You seem to have a remarkably specific question, with budget details - and one of the specifications happens to be that it 'needs to be Windows Server'.
I don't see anything wrong with that, but I'm up for discussion on it.
My feeling is it's not a good fit. For one, we don't do "software comparison" either (see: Is tool x versus tool y a fair question?) – and for the other, it's not asking for "software meeting specific requirements", but "which license should I use for software X" (to keep it abstract).
These are the reasons why I didn't reopen it (though normally I try to be as fast with reopening as I am with closing in such cases): it simply doesn't feel right for me. Others might see this differently, so I'm glad you've brought this up here at Meta. Let's see how the community argues – which I will of course accept then :)