> [...] if the Java 9 and 10 experience is anything to go by, you will be hunting down issues with Maven plugins, transitive dependencies, and libraries holding back for now all day.

You had issues with 10? The only issues I got were with Java 9, because introduction of modules broke some stuff. Later it was just making sure that ASM or aspectj/lombok is in the most recent version that has new JDK version added, which might have been a problem in 10 (I know I was trying to upgrade on day 1).

But nowadays, all the most popular libraries are on par with the next Java version that is in the works at least a month before the release.

Since JDK 12, I just do an upgrade every 6 months and had no issues so far.

And if you don't ship software to clients then there is almost no downsides to upgrading and a lot of upsides.

If you do ship software to clients you should be using jlink, this way you ship smaller binaries and clients don't need to worry about JDK, because you will provide it to them .

And you also need to lookup what LTS means in case of Java - it is not the same as in e.g. Ubuntu.

In Ubuntu you get free of charge fixes in LTS, in Java you need to buy an LTS version from someone (they will make fixes there) OR use the latest JDK version (which gets all the fixes free of charge).

> Guice is one that only recently got the nasty (but relatively harmless) warning you get when using it with Java 11 under control.

Personally I've dropped guice and just stick to Weld anymore since it's the reference implementation of the standard. I haven't had any problems running it on JDK 14.