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gromackFlag for United States of America

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Moving away from SBS 2008...

As the end of life is rapidly approaching, I'm considering ditching my 2008 SBS & moving on to bigger & better things.
Any suggestions on moving to Exchange 2013 or 2016 vs Office 365 & an exchange hosted plan?
Will I have issues taking the currect 20085 SBS out of domain & 'replacing' with an exchange server?
It sounded like a good idea at the time, but I really don't use any of the other features that SBS comes with.
Thanks!
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Thanks for the advice!
I'd love to hear what ecarbone considers "Hosted Exchange" to be - and what service is guaranteeing a 99.999 uptime.

There is no such thing as 100% uptime 100% of the time.  you need to consider what is acceptable to you.  Then weigh the costs.  Whatever e-mail services you employ will be subject to your ISP, the Exchange provider's ISPs, maintenance windows, Microsoft's ability to flawlessly patch things, etc.  I find it silly to expect ANY Exchange provider to RELIABLY provide five-nines uptime for exchange.
Lee,
Here is a link for your pleasure:
   https://www.intermedia.net/products/exchange-hosting

And I never said anything about 100% up-time.
I was comparing 99.99 to 99.999

More knowledge for you here:
   https://en.wikipedia.org/wiki/High_availability

and here:
   https://www.experts-exchange.com/articles/12171/Office-365-99-9-Uptime-SLA-Explained.html
Thank you for clarifying which "hosted exchange" product you were referring to - If you did a simple google you got many different results. For my google results, intermedia is the 4th listed... so it was far from clear.

As for high availability, thanks... I'm well aware of the concept.

and no you didn't say anything about 100% my point was in the rest of the comment:
"you need to consider what is acceptable to you.  Then weigh the costs.  Whatever e-mail services you employ will be subject to your ISP, the Exchange provider's ISPs, maintenance windows, Microsoft's ability to flawlessly patch things, etc.  I find it silly to expect ANY Exchange provider to RELIABLY provide five-nines uptime for exchange."  

According to the EE article you linked to, the following will affect the applicability of Microsoft's Three-nines availability:
-      ‘Due to factors outside Microsoft’s reasonable control’
-      ‘Resulted from Customer’s or third party hardware or software’
-      ‘Resulted from actions or inactions of customers or third parties’
-      ‘Caused by Customer’s use of Service after Microsoft advised to modify its use of the Service, if -      During scheduled downtime
-      ‘During beta and trial services (as determined by Microsoft)’
Some of these may not apply, but you can sure some do.

Further, intermedia's offering does NOT include Microsoft Office which all but the basic plans do.

Odds are, your outages on three-nines or five-nines will be far more than 9 hours per year when you factor in all other possibilities.

And the guarantee is backed financially - I couldn't find the "or else" part of intermedia, but odds are it's not a 25% refund of service fees as it is with Microsoft.  Most SLAs I've seen are daily percentages.

Look, I'm not saying you should or should not go with Hosted Exchange (and Hosted Exchange and Office 365 ARE the same thing when it comes to Exchange - the differences are in the details and what the provider offers as an SLA)  Ultimately you (especially gromack since this is his question) needs to weigh the pros and cons of all services you want to consider.  A big pro of Office 365 is that it includes OFFICE! (in most SKUs), but SLA is a consideration - and HOW the SLA will be honored is also a consideration - as well as support.