Looking for guidance planning the replacement of SBS 2011

What you need is:
Windows 2016 or 2019 standard edition (incl. IIS, Windows Backup, File and Print services, ADDC, DHCP,DNS etc)
Exchange 2016/2019 Standard or switch to Office 365 (much easier and probably cheaper in long term). Supports 1-5 mailbox databases.

Licenses:
https://www.microsoft.com/en-gb/cloud-platform/windows-server-pricing

https://products.office.com/en-gb/exchange/microsoft-exchange-server-licensing-licensing-overview

Just to make sure I'm understanding this while I recover from the shock...jumping from SBS to standard requires us to buy a $1000 license for each user?  That can't be right...40 grand in licensing?!

That doesn't sound right for your small organisation.

Purchasing per device CALs rather than user CALs would be cheaper. Ask a vendor for more accurate quotes.

See
http://woshub.com/calculating-the-number-of-client-access-licenses-cal-for-exchange-server/

"Just to make sure I'm understanding this while I recover from the shock...jumping from SBS to standard requires us to buy a $1000 license for each user?  That can't be right...40 grand in licensing?! "

No, The licence cost is for 1 licensed server (with no more than 16 cores)

Sorry, Peter, I'm confused...are we talking strictly exchange here?  I will probably move to O365 for email.

I have many more devices here than users, so I'm not sure device CALs are the way if it's a 1:1 license.

Edit...ok, thank you Andrew, I can breathe again!

This is what had me worried about the per user cost...

You will still need Client Access Licences (CALs) but they are not $1000 each *phew*

https://www.microsoft.com/en-us/licensing/product-licensing/client-access-license
As Peter says it's best to speak to your current software provider and get a proper quote.

Andrew

Not to beat a dead horse here, but what I'm seeing just isn't meshing here...these screen caps from a large IT vendor we all know and love.

I guess I can just call a vendor and risk being oversold, but is it just me or have they made this more complicated that it needs to be?

Edit:  You beat me to it, Andrew.  Thanks again...I'll figure this out eventually!

Ok, so I do need per user licenses and not just a '24-core' license...but yeah, the cost isn't quite $1000.  :)

Last one before I go back to some independent reading/researching...

Any input on the RDP feature...I know I won't have the same simple web based OWA option, are people just going 3rd party these days?  

RyanIrish,

Without SharePoint in the mix is there any SQL or need for database backends?

The starting place is:
 * VM0: Active Directory, DNS, DHCP (2 vCPUs and 4GB vRAM)
 * VM1: File, Print, and Database Backends (2 vCPUs and 4GB vRAM to start)
 * VM2: Exchange (4 vCPUs and 16GB vRAM to start)
 * VM3: RD Broker/Gateway/Web and possible Session Host

We've done lots of SBS 2011 Standard and Premium to the Microsoft Stack keeping Exchange on-premises. The main thing with Exchange is that the install requires .NET compiling on-the-fly but once in place it can generally run on the above specs.

Licensing required:
 (2) Windows Server Standard 16 Core licenses (assuming physical box has 16 cores or less)
 (30) Windows Server Use CALs (or mix and match with Device if shift work per PC)
 (1) Exchange Standard License
 (30) Exchange Server User/Device CALs

NOTE: We just won a competitive bid against an IT firm what wanted mail and collaboration in O365 and our cost per user per month was less. So, it is _not_ less expensive.

Hi Philip,

SQL...that's a good question, and something I hadn't considered yet.  Outside of the SBS monitor, I don't know that anything else is using.

KAV_CS is a remnant of Kaspersky, and the BKUPEXEC is probably from an old install of Symantec...

I do have our door access system on this server, that might depend on SQL.

Can I assume that anything SQL dependent would show up on this list in SQL management? 

Looks like I will need SQL afterall.

RyanIrish,

The SQL version and edition is probably something the vendor supplied. More than likely it's the freebie "Express" edition.

So, here's a slightly revised version given that there's 30 users I'll bump things up a bit since I don't know the whole story as far as overall data and I/O needs:

 * VM0: Active Directory, DNS, DHCP (2 vCPUs and 4GB vRAM)
 * VM1: File, Print, and Database Backends (2 vCPUs and 4GB vRAM to start)
 * VM2: Exchange (4 vCPUs and 16GB vRAM to start)
 * VM3: RD Broker/Gateway/Web (2 vCPUs and 4GB vRAM)
 * VM4: RD Session Host (RemoteApps and Session Host Desktops) (4 vCPUs and 16GB-24Gb vRAM)
 * VM5: SQL, MySQL (Sage/Intuit/ETC), and other active database backend (4 vCPUs and 8GB-16GB vRAM)

License Needs:
 (3) Windows Server Standard 16 Core licenses (assuming physical box has 16 cores or less)
 (30) Windows Server Use CALs (or mix and match with Device if shift work per PC)
 (1) Exchange Standard License
 (30) Exchange Server User/Device CALs

I bumped up the license count by one to allow for up to six (6) virtual machines.

EDIT: Physical server setup would be the next step.
EDIT2: SQL instances are listed in Services.MSC

The door access software will probably run on SQL Express Edition (especially if it's Paxton Net2).

Many thanks for the continued advice, you guys are awesome.

Welcome to the fray, Lee!

So I hadn't planned on virtualizing anything as I figured that would just add extra layers of complexity (and cost) to a project that I'm already less than confident about...but it seems I need to reconsider.  

We are on the standard version of SBS, and so I'll assume the free version of SQL will suffice for the door access, which is CardAccess3000.

Cost is definitely a factor.  I would probably rather spend a bit more on performance and storage at the expense of additional VM's.  If the only real benefit of the extra VM's is reduced risk of restart disruption, I (they) will have to live with the rare reboot during production hours. Your version of 2 VM's may be a better fit for us.  I really don't like saying one opinion offered is better than the next, as I don't have the experience or knowledge to do so, but I do need to avoid overkill and cost creep where possible.

As for storage, I'm at 845/2000 gigs of storage now, but much of that is going to exchange.

You're the first one to mention my lack of experience, and you're 100% correct...the idea of attempting this solo is costing me sleep.  If I had a server that wasn't crashing daily ( https://www.experts-exchange.com/questions/29174927/SBS2011-crashing-rebooting-with-Event-41-Kernel-Power-error.html ) and driving my users crazy this would be a different story, but I feel like I'm on borrowed time already.  I've been going back and forth on trying to find a consultant or just buying a migration guide from a site like server-essentials, which at a glance seems to offer pretty thorough guides.  

As for the network, I'm sure you all would consider it very simple.  Two physical servers (SBS and ERP), a few unmanaged switches and a bunch of workstations.  I do have two locations connected by IPSEC, but the remote location has only clients, no servers.

The more I read and learn the deeper this hole seems to get!!  I don't want to go overboard with the gratitude, but you all have no idea how much it helps someone with my experience/skill level (lack thereof) to have a place like this to seek out help and advice...thank you again.