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Is it known whether NET 5 will require new VS version (ie. 2021)? I'd love to upgrade to net core 3 but I don't want to upgrade everything again in a couple of months.
I'd guess that it would require a new version of VS. To use .NET core 3.x you have to have VS2019, that is unless you're using Rider.
.NET Core 3.1 is a LTS version. It should be good for a while (3 years I guess).

If the dev env upgrade burden is a topic, go for the LTS versions.

We had a lot of pain upgrading to .NET core 3.0 and 3.1, there were some subtle breaking changes (like dotnet build doing a restore whereas it didn't before, causing nasty runtime issues with platform dependent dependencies like SqlClient). If you haven't done the upgrade yet, plan plenty of time for it, and smoke test the heck out of it before you go live.

Also ensure you're on the latest (1.1.1) version of SqlClient if you use SQL Server.

That seems really short lived! The upgrade sounds like it's going to be a bit of a headache too.
Non-LTS releases are supported for three months after the next version has been released. 3.1 is supported for quite a while longer.
Looks like X.1 releases are the way to upgrade in .NET Core. I don’t know why I never found out that X.1 series are the LTS releases.
That's just been the case for 2.1 and 3.1, future versions will jump a version each year (next is v5) with every other year being LTS. Of course, we'll see if it actually goes as planned. I don't think I've seen them change course from the announcement last year.

https://devblogs.microsoft.com/dotnet/introducing-net-5/