We are very excited to get our hands dirty with .NET 5 sometime in Q1 next year. We currently run on .NET Core 3.1. I expect our migration from 3.1=>5.0 will be a total non-event, but we don't want to risk any regressions during our current crunch phase. Our migration from 4.7=>2.0 was the most difficult, but once we got everything off Framework and onto Core things have been going really smoothly with the incremental upgrades. Really hoping this trend continues indefinitely.
The only part of .NET 5.0 that has left me disappointed is the continued lack of polymorphic deserialization support in System.Text.Json - a la Newtonsoft.Json's TypeNameHandling enumeration. This is the only thing holding us back from migrating to this first-party dependency. I have already left feedback regarding our use case in the appropriate dotnet/runtime GH issue.
The biggest new features I am looking forward to are the performance enhancements surrounding startup time, GC, etc. Improved P95 latency is something that will be very welcome in some of our busier environments.
In terms of the overall package that .NET brings to the table, we couldn't be happier. Sure, VS could run a little smoother and some of the configuration/DI stuff can be very aggravating (at first), but overall its a fantastic experience.