I would echo what others said. It depends on your user base and what your needs are. Are you going to need web access only ? are there a number of outlook users ? Android ? iPhones ?
We only have about 200 users on our server across about 15 domains. I dont think anyone of them uses outlook to sync, or syncs with iphone mail or android mail. as far as i can tell, almost all 200 users access their email through the web interface. With taht said, we rarely have any issues at all. And the issues we do have from upgrading, are same as what Matthew just said, our installation has been upgraded over and over, we started on Ver 14 about 10 years ago, and upgrade after upgrade, occasionally we have something from the old version data that creates issues with the new version software.
We are currently on 9014 and no issues reported to us at all,
www.HawaiianHope.org - Providing technology services to non profit organizations, low income families, homeless shelters, clean and sober houses and prisoner reentry programs. Since 2015, We have refurbished over 11,000 Computers !