I'm comfortable with MacOS upgrades. They have always worked for me. I upgraded my 2014 Macbook Pro and didn't have (or expect) any problems. I say do it.
If you're running anything special. Razer Synapse, Citrix Receiver, etc, it's good to double check their support sites before upgrading. I have Parallels and installed Sierra on a guest VM first and checked out the critical functions, both of the above had issues. Citrix was fixed, for the most part, within 2 weeks. Razer is still hosed. The OS itself is great just be careful about the surrounding software.
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So I have an early 2015 Macbook Pro 13'' curently running El Capitan 10.11.6 I'm a bit nervous about upgrading to Siera, as I always seem to loose something or get a glitch. I'm probably over reacting right? just upgrade? Anyone do this upgrade? any pro's or cons? TIA BTW everything has been backed up.