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I'd say that Java 8 -> 11 is going to be and order of magnitude more disruptive than 11 -> 17.

So if you have downtime now (ha ha), you might as well migrate to 11.

Why not put all versions of Java, including the master branch build, into your CI, then you can instantly see what it's possible to upgrade to, and instantly see when incompatibilities appear.

I don't really get what migration issues people experience in practice.

upgrading from 8 to 11 is a good step to have. You will not believe how many problems pops up. Upgrading from 8 to 17 might be a very hard exercise - libraries and all..