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There are a zillion Xeon processors -- how does anyone go about making a decision?
Doesn't seem like either Medware or AC really make huge demands on hardware, at least, not in a small office. Reliability is the main issue.

Depends on the demands of the user. There are 2 main sockets you should be looking at. (LGA 1155 Mid Range and LGA 2011 Enterprise Range)

That E3-1225 is the Mid Range (Ideal for single OS computers/servers). I'd see if you can find one with the E3-1230 or higher. E3-1230V2 Preferred. There are higher models like the E3-1270 which are a $100-$200 for an extra .1 GHz of Performance. There is little to no real world difference between the E3-1230 and E3-1270. The reason I recommend the E3-1230 over the 1220/1225 is that it has hyperthreading. (Looks like 8 cores instead of 4). These are great for Windows 7, SBS Essentials, SBS Standard. Very fast and good price. (Equivalent to i7-2600)

E5 Series CPUs are for LGA 2011. Get these if you plan on expansion. I.e. going to need a server that needs more than 32GB of RAM or if you are going to be running multiple virtual machines. (e.g. SBS 2011, Terminal Server (for iPads/thin clients) all on one server) These are "real" server boards. These are very pricey though (~$500 for dual socket). E5-2620 are hexacores and a good price point ($400) if such a setup is necessary. (Equivalent to i7-3930K)