Kullbee Sperado, backwards tailslide, and contraband cybernetics

[wootywoo13]

Kullbee Sperado, who has backwards tailslide and contraband cybernetics equipped, activates with s-foils closed, and spends the charge for contraband cybernetics.

With his s-foils closed, he performs a 3 straight, near a debris cloud. Kullbee decides to focus->red boost over the debris cloud. He doesn't overlap. Can he then gain an evade token (s-foils closed, after boosting/barrel rolling over an obstacle, if you are not overlapping the obstacle, gain an evade token), use his ability to open s-foils, roll for crit damage from the debris cloud, and end activation with 2 stress tokens, one evade token, and one focus token?

If he started the activation phase while stressed, would the same result occur, but with 3 stress tokens (already stressed, contraband activated, s-foils closed, 3 straight, focus->red boost over debris cloud, check for crit, open s-foils?

Also, would this combination only work for debris clouds vs asteroids or gas clouds? 

Thank you for your time and effort, appreciate your work you put into answering these questions.  

[Kris M]

There's a few things happening here, I'll do my best to keep this clear.

Yes, so long as Kullbee Sperado boosted or barrel rolled THROUGH the obstacle, and is not at range 0 of it once the move is complete he gains 1 evade token. Because he performed a boost or barrel roll action, his pilot ability would trigger, allowing him to flip an equipped configuration upgrade card. He would then suffer the effects of overlapping the obstacle. 

In this example, he would finish with one evade token, one focus token and 2 stress tokens (one from the red boost action and one from overlapping the debris cloud). Note that Contraband Cybernetics is not required to achieve this, as the evade is "gained".

If he were to begin the round already stressed, he could trigger Contraband Cybernetics and perform the same set of maneuvers and finish with a total of 3 stress tokens. And finally, the effects he would suffer would depend on which obstacle Kullbee moves through, but there is no reason he could not do this through any of the available standard obstacles.