Daniel,
We are experiencing the same issue on the same versions of Java and BP as Andrew. I'm not sure that I completely understand your explanation. If the path to the element is too long why does it always work on the first attempt to spy, regardless of the element, after restarting BP? Shouldn't it fail on the first attempt?
Also, unless I am misunderstanding your solution suggestions, they both seem to indicate moving toward more of a surface automation approach as opposed to standard application spying. This is not desirable if we can avoid it. Any other suggestions?
Thanks,
Tony