I think this is an interesting question. Does the 'done out of steps' criteria explicitly necessitate increasing the difficulty of the jump itself? Since it appears that it is subjective what makes a jump more difficult for different skaters and also for what type of jumps, should the judging of the GOE actually include perceived increase or decrease in difficulty of execution?
There are two different bullet points that could apply:
1) unexpected/creative/difficult entry
2) clear recognizable (difficult for jump preceded by steps/movements of the Short Program) steps/free skating movements immediately preceding element
If the skater is doing something that many skaters have done before (e.g., running threes into a loop jump ever since Slutskaya popularized that entry 20 years ago, or more recently choctaw-choctaw on shallow edges heading into a lutz), the steps would no longer be unexpected or creative as would have been the case when such entries were rare. But even that could be debatable, because some judges might see a lot of skaters do it at the competitions they judge and watch on video for pleasure or learning, and others might not have seen it very much and still consider it creative.
"Difficult" will also have borderline or gray areas for different judges, in part based on what was easier or harder for them in their own skating experience. Or just thinking "Well, it's a little more difficult than a plain vanilla entry, but is it enough added difficulty to merit a bullet point?" If it's something unusual but not particularly creative, each judge would have to make that decision for herself.
As for the clear recognizable moves immediately preceding the jump, the requirement is just that they be immediately preceding, not (in most cases) that they be difficult. By nature, BO-FI-BO three turns into a loop will immediately precede the loop, so they meet the immediately preceding requirement.
Anything where there could be pause in the rhythm between the steps/moves and the takeoff to allow the skater to reposition the body before jumping, if the pause is more than a second or so it would not be immediate, but it could be difficult.
So difficult moves . . . pause . . . jump could earn bullet point 1. (So could a creative approach even if it's not very difficult.)
Easy moves immediately into the jump could earn bullet point 2.
Unless it's the short program jump out of steps, in which case the preceding steps are a required part of the element so they don't earn bullet point 2 unless they're difficult, and a significant pause would be cause for a -1 or -2 reduction, which could cancel out bullet point 1.
The recommendation is two positive bullet points for +1, four for +2, six or more for +3.
If both of those bullet points apply (difficult
and immediately preceding, or unexpected/creative and immediately preceding for anything but the SP solo jump), then a +1 is warranted, assuming there's nothing negative about the rest of the jump. If the entry earns two bullet points but then there are problems with the air or landing phases, then the negatives could cancel out the plus and the jump could end up with 0 or -1 or -2 after subtracting the appropriate reductions from the +1.
If only bullet 1 or bullet 2 applies but not the other, then there should be something explicitly good about the rest of the jump (bullets 3-8) to qualify as +1.
Easy, unimaginative steps or moves immediately preceding a just-adequate jump would only earn one bullet point -- none for the SP solo jump -- so in that case the GOE should probably be 0.
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