SBS 2011 standard migration to windows server 2016 essentials - Advice please

SBS 2011 standard migration to windows server 2016 essentials - Advice please

I've been tasked with upgrading a SBS 2011 Standard server with Windows Server 2016 Essentials on new hardware. At present, the client has 12 users, running the server as file storage and on-premise Exchange 2010. Customer does not use SharePoint. Customer would like to migrate to Exchange Online.

This customer is new to me so I don't have the benefit of the current server’s history or any past/potential problems that have or may occur.

I would like your advice on the best (least problematic) way forward. Do I:

1) Migrate on-premise exchange to Exchange Online. Once complete, disable on-premises exchange services. Leave for a week to ensure email is okay and client happy. Then either:

a)      Create brand new domain using windows Server 2016 Essentials and join clients to new domain.
b)      Migrate SBS 2011 Std to Windows Server 2016 Essentials

If I migrate, is there a chance of bringing problems over from the old server (if any exist)?

I welcome your thoughts/comments
LMG09Asked:
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Cliff GaliherCommented:
Unless you have a very good reason to rebuild, I recommend migrating. Rebuilding basically means new user accounts, new profiles, a need to touch every desktop, and user interruption.

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LMG09Author Commented:
Thanks for your prompt response - Is there any possibility of bringing over issues (e.g. incorrect/corrupt setup) from the old server to the new server?
Cliff GaliherCommented:
That rather an open ended question. And the answer is "it depends." It depends on what was misconfiguration or corrupt.
LMG09Author Commented:
Thanks for your prompt response. Unfortunately, it is an open ended question because I've not been able to a assess the current server in detail yet. I've decided that migration is the way. Once again thanks for your input.
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Windows Server 2016

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