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I love this topic and discussion. I wish I had gotten in on it sooner. Though the OP has decided to pursue a different route from on-premise hardware, I'll still share a few thoughts. If one is going to buy a box to act as a web server, I would second the recommendation to use it as a VM host, with the web server being a guest. If the local infrastructure does not already have server virtualization at its core, and you're looking at having just 1-3 physical boxes, then VMware might be a bit much, both in terms of complexity and scale (as it's designed to handle rack upon rack full of nodes), and cost (likely to be applicable in any case -- especially now, since VMware changed its licensing model for vSphere 5). For the past two years, I have been managing several VM hosts running Ubuntu as the base OS, libvirt as the management layer (which has a quite extensive API), and KVM as the hypervisor. It even does a great job running Windows Server guests. Perhaps I have a bit of a bias, but I would definitely say that this combination is mature enough (especially in Ubuntu 12.04) to compete with the likes of vSphere, XenServer, and Hyper-V. I could go on and on here, so I will summarize some more considerations as to not TL;DR. - current and anticipated workloads (can be estimated through good monitoring of existing servers) - capabilities of the VM host hardware (or, why that 7-year-old box might not be a good candidate) - network infrastructure - storage, storage, storage - special hardware needs (e.g. physical security keys) Virtualization is not exactly off-the-shelf easy. For the uninitiated, it takes a few tries to tune the hosts just right. For local, on-premise control of servers, though, it is worth it.