SBS 2008 to Windows Server 2016 - Migrate or Fresh Start?

What would be the best route to move from SBS 2008 (Exchange 2007) to Windows Server 2016? (Mail would be hosted  by Office 365) Its a small environment of 10 users. Perform a migration to the new physical server or start fresh with a new domain & then join all PC's to the new domain?  If its the latter, what would be the steps? Would the new server get joined to existing domain as a member server? Also have to think about moving user data stored in each of their profiles.
yohayonAsked:
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Scott CSenior EngineerCommented:
If everything is running and stable in the current environment, then I wouldn't see any reason to not migrate.  It will be much easier on you.

Of course, before you start, make sure you have a good and tested backup of your current server.

Just configure the new 2016 server to be a member server and then make it a DC.

After that do your email migration and then decommission your SBS.

The one thing to be aware of is when you transfer the FSMO roles a timer will start and after some days, your SBS will start rebooting itself.
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Scott CSenior EngineerCommented:
As an aside, if you've never done this before, give it a try in a lab.  If you still don't feel comfortable, you can create a Gig here to hire someone to do the work for you or fine a local professional who has done this before.

It's not hard if you've done it before, but if you haven't things can go sideways quickly.
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yohayonAuthor Commented:
Thank you very much. I have heard many say that it may not be a great idea to migrate due to the extra garbage that a migration will bring into the new server. If I want to contemplate a fresh start & not a migration, what steps do you foresee for this scenario?  Would the new server get joined to existing domain as a member server? Also have to think about moving user data stored in each of their profiles.
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Scott CSenior EngineerCommented:
I see a lot of work and lost data.

I don't know who these "many" are, but they don't know what they are talking about.

If you have a good, stable, clean environment, then a migration is the way to go.  

If you do a fresh start...not my recommendation, then you would NOT join your new server as a domain member.

And since you asked that question, my further advise is to get someone who has done this before.  Asking the question you did tells me you do not have the necessary experience.

No offence intended, just my professional observation.

Just estimating from the information you provided, this is a 16-24 hr. project.
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Scott CSenior EngineerCommented:
I have done quite a few of these and the only time I had to do a fresh start was due to the SBS environment not being stable and AD ripped itself apart.

That's why you want someone with experience doing this, if things go bad, they can recover quickly.

In my case, I was able to keep the company working and each user only lost a few minutes when I moved their machine to the new environment.  Also, in that case I had to pull in my entire team to assist me.

But typically migrations are the best way to go.
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yohayonAuthor Commented:
Thank you for your technical input relating to the questions asked. Your other comment based on your own "observations" is unnecessary & uncalled for.
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Scott CSenior EngineerCommented:
With the information you provided, I don't believe it is.  I didn't mean any offence, but if you took it that way I apologize.

You asked if you should join the new server to an existing domain in order to do a "fresh start".  Those two things are mutually exclusive.  If you join the new server to the domain you are committing yourself to a migration.
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Hypercat (Deb)Commented:
Just putting in my 2 cents worth to agree with Scott.  I've done these migrations as well, and as long as the existing SBS Active Directory is in good shape, a migration works much better than creating a complete new domain and trying to move things over.  Here's a very good article that I've used to help guide me through:

https://www.itpromentor.com/sbs-ad-mig/

He mentions adding the "Essential Experience" role, but if you want to just migrate to a 2016 Standard Server domain, then you can just skip the step to add that role.
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yohayonAuthor Commented:
Wow! Thats a fantastic article that spells it all out from start to finish. Thanks a lot.
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Hypercat (Deb)Commented:
This page has links to additional steps for migration of printers and file shares and then removing the SBS server from the domain:  

https://www.itpromentor.com/2016/07/
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Lee W, MVPTechnology and Business Process AdvisorCommented:
yohayon,

If you took offense to Scott recommendations, you'll hate mine.  

I think this is relatively easy to do in EITHER case.  A migration OR a clean install.  But that ease comes with experience and understanding of the technology.  When you lack that experience and understanding, things become an order of magnitude more difficult.  At least.  No one is questioning your ability to learn - but if you lack the experience of domain migrations and the understanding of how the technologies work, the time you SHOULD be taking to ensure you do it right and don't potentially damage your organization's ability to work will be excessive compared to the cost of a professional who can do it for you and provide you with best practices, implementing all the technologies that can help your environment work as productively as possible.

That said, for an environment of 10 users, where you can control everything, using a tool like the User Profile Wizard and setting up a new domain over a weekend can be done.  Doing it right will take a professional between 20 and 40 hours depending on how your environment is currently configured and how you want things to work when complete.

Doing a migration can take less time, however, I personally don't like domain renames and I especially don't like .local domain names so this would be an opportunity to change that things.  It also ensures everything starts clean, though if you haven't mucked about with Group Policy much on your own, cleaning up the SBS group policy isn't that big a deal.

No matter what, you should be virtualizing.  And if you insist on risking your organizations ability to work, I strongly encourage you to run through the ENTIRE process in a test environment AT LEAST twice.
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