This is a question to help make a decision based on the Microsoft stack.
Once biz spark is over, how will the licences cost for stackoverflow? 2 db servers 5 web servers at last count?
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You should look at SQL Server licensing costs first, which are incredibly expensive.
Windows Server licenses are quite inexpensive in comparison. SQL is what gets you. I mean, SQL Server licenses are "if you have to ask how much it costs you can't afford it"1 expensive.
It's particularly irritating that Enterprise edition is the only version of SQL that can do live (online) index rebuilds, for no technical reason whatsoever. Purely a market segmentation marketing weasel "feature".
read and weep.
1 aka "bend over"
It's not cheap. But the idea is that either (A) your business is successful and you can afford it — I get the impression that StackOverflow isn't too worried, for example — or (B) your business failed, in which case you just stop using the product and owe nothing.
Personally, I think most of us still need to worry about option (C) where you're still just limping along and hardly have any spare cash. But if that's the case at least you probably still have everything on one server, and perhaps you can manage with something like the Express Edition of Sql Server.
This is probably where SPLA licensing comes in to play. We use it to cover some 60+ machines for a SaaS environment.