If you are happy with the v14 Web interface, might I suggest that you upgrade to v15 for now. 

There are more outstanding issues with v16 than there are with v15. There are a couple of features in v16, however, that you might want, so the choice is up to you. 

Thx that might be good advice.  We have no issues with the web interface currently and I'm not planning on looking at v17 until its been out in the wild for at least a year.

I upgraded a client from v11 to v15 not too long ago, and there were very few issues. 

Had to re-configure IIS and reinstall SSL certs* because it was on a new machine, but that was a given. The IP addresses and bindings were reset for the new server after SM was started.

BTW it appeared to me that SM used the lowest IP address on the NIC for outgoing email instead of the one set in SM, with Server 2012 R2.

One of the biggest issues in the upgrade was that I had to re-check the box to enable Active Sync for EAS users. Not a big deal at all.

 *turns out it's fairly easy to export your cert. from IIS and import into the new server if you know the procedure; given that the cert. is up to current standards.

Hi Matt. Going from 14 or 15 to 16 is a very easy and straight forward process. As Paul said above, if you and your customers are accustomed to the 14 interface, then you will probably want to upgrade to 15 as it is the same. Version 16 comes with a completely revised webmail interface which may cause your users to have a learning curve which will equal more support time spent helping them. Also, again as Paul said, 15 has less problems than 16 at this time. If you have any questions about your migration, please post them here or email me directly at the address in my signature and I will be happy to help. I do several migrations per month and rarely have issues. Good luck! Take care!

Thanks to you both!

Indeed, Linda was a great help for my SM migration as well! Credit where credit is due.

Thanks so much Paul!