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I upgraded a late 2014 iMac 5K over the past weekend. Everything so far has gone quite smoothly.

As joemikeb mentioned, some apps will require additional security allowances. But I found that process to be very straightforward and many of the app developers provided instructions on what was required for their specific application.

My move was from MacOS 10.13.x. You may find a two level upgrade (i.e., from 10.12.x) a little bumpier, but you are not the only one to be making that jump. From what I have read, many people are saying this is one of the smoothest initial upgrades of any OS X.

Also, based on other comments in this forum, I am using Dark Mode and liking it.