I have had very similar issues with helmets! I used to have a wild country 360 and had a similar problem with getting it to fit and sit straight as I have a very small, apparently unsymmetrical head.
After trying on many different helmets I now have a climbing technology stark helmet and similar to JoW (although a different version) I find it much more comfortable and have had very little issues with it. The wheel which resizes it did get jammed once but it's just had some cave grit wedged in it which was easily cleaned.