Opinions wanted: Windows server upgrade help!

We are a small business of 50 users, (4 offices). We run two 7 year old DELL servers: #1 SBS 2008 with Exchange 2007, #2 Windows 2008 Terminal Server (25 users on it). Lately servers are buggy, periodic Application freezing on Terminal Server and SBS Server is slow (takes minutes to open programs and boot time is ridiculous 50 minutes!

I am sourcing one replacement server and will visualize the server OS, and re-install Windows server, Active Directory etc. from scratch.

What I am unsure of is whether to re-install Windows SBS 2008 (we own it and CALs) and re-use for another 6-7 years
OR
bite the bullet and purchase new Windows 2012R2 and Exchange and start completely fresh. (or maybe host email via. Office 365?)

Any suggestions anyone?

Thanks so much,
Steve
shood4012IT ManagerAsked:
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David Johnson, CD, MVPOwnerCommented:
from the symptoms presented you probably have a failing hard drive. Use the disk manufacturers diagnostic tool and test
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Larry Struckmeyer MVPCommented:
Also, long boot times can be DNS settings.  For SBS the ONLY DNS server under ipconfig /all should be the ip of the SBS itself.  This is also true for all the clients.

Also very with treesizepro or windirstat, run as admin, that the system partition has at least 20% free space.  25% is better.

As for direction going forward.... SBS 2008 is a known OS.  It fits your skill set.  As you say you own it.  otoh it is nearing the end of life and will be out of support before your suggested 5-7 years.  

If time is a problem for you in getting all this done, assuming you decide to do it... I would consider ordering the new box but not with OEM software.  (trial or Open License with or without Software Assurance).  Then I would install your Windows 2008 as hyper-v and install SBS as one VM and Server 2008 again as RDP both as VMs.  If the OS is not the problem you could P2V it, all this assuming they are not OEM and tied to the old box.

Next I would install a couple SATA drives in the old box and install Server 2012 R2 trial so as to play with it.  Once familiar with it, then you could make the switch.  The primary consideration is the email.  If it still lives on the SBS you need to make arrangements for where to host it once the SBS is gone.

Also keep in mind there will be a new version of Server in the next X months (no one knows for sure when).   That might be worth waiting for if you can nurse the SBS and 2008 servers along, either as exist with some repairs or as VM's or  on new hardware.

http://www.microsoft.com/en-us/evalcenter
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shood4012IT ManagerAuthor Commented:
Hi Larry wow that is great answer,  I thank you for that,  very much! Dns appears to be OK,  just SBS IP. Have 100gb free in SBS system partition,  this is 50%. As these servers aging and we don't do replication,  only daily images backups...  have decided to proceed with new hardware. As 2008 end of life only 4 years and exchange 2007 just 2 years I personally feel best to start fresh with 2012. I would use outside IT company to assist me with setup. Does it make sense to leave 2008 given short life span? Also,  my copy of SBS is from Dell and is oem,  no windows stickers on my servers.
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Larry Struckmeyer MVPCommented:
Do the drive test as suggested above and while you wait for the new hardware update and run the SBS BPA and fix anything it finds.  Examine the event logs for any errors and see if any require attention.

If the DNS is actually running on the SBS the long boot times tell me services are not starting promptly.  From msconfig disable anything in services and startup you can live without for a test... yes including exchange restart and see if the behavior changes.  Then enable services in the 50-50 method until you find the one(s) that are the problem.  Let us know the result.
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