So I should look for a Dedicated VPS or a Dedicated Server? What the difference between the two if there is? Can you suggest a company that suits my needs listed above?
honestly, you should be looking at a real virtualized instance with its own full OS install. A dedicated server is not useful these days with these sorts of minimal requirements. Plus with a virtualized server, you would typically be on much better hardware - faster CPU, RAID10 drives, redundant components, etc.. just get a VM using real virtualization technology like xen, vmware, kvm, etc.. and avoid things like virtuozzo or openvz (which is more like shared hosting). there is zero reason in this day and age to get a dedicated server for a requirement of 2GB RAM. its an inefficient use of resources, bad for the environment and you can never get the same overall value
He should be allright if his VPS is on a server with good uptime.
Generally i don't see a Windows VPS could go down too often unless the host is very bad.
Resource on Windows VPS cannot be oversold at crazy level like Linux.
VPS could go down only when there is hardware problem or network problem which do not occur very often.
Bad neighbors may cause trouble as well.
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