1.My settings are the default recommend core.autocrlf=true. Probably best not to tell users to stray from that. The windows git installer and all guides I have seen recommend this.

I wouldn't suggest getting users to do anything; just add a .gitattributes file (in source control) to the org.hibernate.test.fileimport package directory, as suggested by Jocki. I can see that this could be a bit fragile though or possibly cause further confusion.

2. Would it make more sense to inspect the file at the start of test to determine the line ending style rather than relying on the env which as you say would be different based on the got config?

I'm happy to give this a go sometime this week and see what I can come up with (also happy for someone else on this ticket to do so if they get there first). May be it would be neater to have a file somewhere containing only a line-ending and refer to that?

3. Is this one specific test valuable enough to be a barrier/pain point for windows contribution?

Very good point!