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How many can you pack on the server or are we talking quality?
This totally depends on the configuration and if your templates has been/is going to be optimised
Assuming ESX (because it makes no sense to run anything else for this) with an over commit of 1.5 and 2008's minimum ram requirements of 512mb you can get around 384
Obviously that's pretty much idle or light use, I suspect your processor will be an issue before ram in terms of number of VPS you can run and your disks better be ssd raid 0 or 10.
The issue on Windows VPS is I/O speed. It can be mitigated with staggered boots and carefully customized Windows update policies, but disk I/O is the primary bottleneck, usually. SSD helps, and a large controller cache is required to buffer read operations. As alternative, VPS memory need to be increased to at least 2 Gb to reduce disk trashing. If the VPSs are doing a lot of traffic, the NIC may become the bottleneck. I would say that Windows 2008 is not the best choice for a high density installation. Windows 2012R2 has better efficiency.
quantity wise : 50-60 assuming each vps has 10gb disk and 1gb ram
quality wise : 20 at most.
optimized configuration should give you a hundred or so pretty good quality VMs but bottleneck will be NIC and disk i/o
Your bottleneck will be i/o. Windows vms need a lot of dried performance to run well.