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The BIND DNS server has already been deprecated and removed from Plesk for Windows.
If a Plesk for Windows server is still using BIND, the upgrade to Plesk Obsidian 18.0.70 will be unavailable until the administrator switches the DNS server to Microsoft DNS. We strongly recommend transitioning to Microsoft DNS within the next 6 weeks, before the Plesk 18.0.70 release.
I would say at least Windows Server 2003 Standard Edition (with SP1). SP1 has some serious fixes.
Why Standard and not Web? Because in future, you might want to install Microsoft SQL Server. In Windows Web Edition, SQL Server is not supported, you can't install it. So your only option would be to offer MySQL to your customers, not MSSQL.
CALs are Client Access Licenses, you don't need to buy any extra unless you want to connect to your server remotely with more than one person at once (Remote desktop, not viewing webpages).
The only advantage to using Enterprise is it supports clustering and more processors/ram. Windows clustering doesn't mean anything to PSA, so its a good waste of money IMHO.
We use Web Ed for our servers. While you can't install Exchange or SQL on Web Ed, if at some point we needed SQL server, we would load a new server specifically for running SQL. If your to the point where you need SQL, you don't want to run anything else on the same server with it. Until then, DE and MySQL are enough for most.
Aside from not running large enterprise apps like SQL or Exchange, Web Ed is the same as Standard.
****NOTE****
If your going to use Windows for hosting, the OEM EULA that comes with the cd does not apply to you and is void by your environment (reselling windows services for profit). You have to contact MS and get Service Provider licensing. This also goes for buying new servers with Windows (i.e. Dell, HP, etc) as the OEM EULA is targeted for use on internal networks. AFAIK, this doesn't apply to servers you get from The Planet, ServerBeach, etc..
one more thing to consider... Enterprise allows for more RAM and CPU..if you have a low end server then Web or standard should be fine.. If you have a Four CPU server (maybe even two with Lots of RAM) you should consider enterprise. For example..if you want to have a server with 6 Gigs of RAM you will need Enterprise to take advantage of it, or if you are considering upgradeing the ram to more than 4 in the future..only Enterprise will support it. We run Enterprise because we run PLESK under Virtuozzo for Win (now ver 3.5) with only 2 CPU's and 4 gigs of RAM at the moment, but the server can be upgraded to 12 Gigs so we are thinking ahead as we add more Windows Plesk VPS's under virtuozzo...
Contra:
Web Edition -
a). Cannot be DC (future versions of Plesk will able to install on DC)
b). MS SQL cannot be setup (using preinstalled MSDE)
c). CPU and Memory limit (2 CPU, 2 GB Memory)
d). Cannot install terminal services (used for Virtuozzo)
Standard Edition -
a). Price (expensive then Web Edition)
b). CPU and Memory limit (4 CPU and 4 GB limit - for future use of Virtuozzo)
Enterprise Edition -
a). Price (expensive then two mentioned above)
b). More complex in management
Pros:
Web Edition -
a). Low Price ideally for low-end web hosting
b). Specially optimized for web hosting
Standard Edition -
a). Support MS SQL Setup
b). Can be domain controller
c). Can install ISA (security reason)
d). Can install terminal services
e). Can instal Network-Load-Balancing (currently no relation to Plesk)
Enterprise Edition -
a). Support MS SQL Setup
b). Can be domain controller
c). Can install ISA (security reason)
d). Can install terminal services
e). Can instal Network-Load-Balancing (currently no relation to Plesk)
f). Up to 32 GB Memory and 8CPU 32bit. Up to 64GB Memory and 8CPU 64bit (ideally for Virtuozzo ---- the first part)
g) Supports 8 node clustering included SAN and geographically dispersed clustering (currently no relation to Plesk)
h) Supports WSRM (Windows Server resource management) - each task can be assigned CPU usage percent
Take a look and make a choice
CAL is Client access license. Not used for web connections. Used in enterprise to count clients which use server for various tasks (from file server to DC)
Also you can install this one, but it is not the better solution, because SBS tries to install AD by default and Exchange 5.5, if you are not skilled administrator, you get a lot of trouble while configuring it for Plesk.
Difference in nature, it is good "All-in-one" solution for SOHO (AD, firewall, Exchange, file server), but is not a better one for web-hosting provider
Also, unless you are putting all this on a server in your own company, you're not allowed to use a OEM/Retail version... if you put the server at a co-location, which I assume you'd do if you're planning on hosting, you need to get a different Service Providers License from Microsoft (or a company that sells them)... then you pay a monthly fee, usually.
You're not at all allowed to use OEM anyway, unless you're buying a new PC (or new piece of hardware, but that's a grey area when it comes to legalities).