the Dharma protector can clear obstacles in multiple ways. The basis of the clearing of obstacles are not obstacles so that we can live a better life or have a more comfortable life, but obstacles towards our understanding and practice of Dharma. If us winning the lottery will bring us further away from the Dharma, then we will not strike lottery if we were meant to because that would bring us down instead of bring us benefit in the Dharma. the protector will make sure we will not get that lottery ticket because it will only lead to more suffering in the long run since by nature it does not bring us closer to ultimate happiness which is the practice and study of the Dharma. If we are to experience a difficult situation and only emerge to be stronger in the Dharma due to that, the protector will make it so that we experience that difficult situation but we will somehow not sustain any permanent damage but we will emerge to be stronger people. Clearing obstacles does not mean that the obstacle will be 'removed' on the surface, but sometimes it could mean that the protector is helping us to gain the strength to break through this obstacle and many more other obstacles. That is how I would see it and that was exactly what I have experienced before.
I have made prayers to Dorje Shugden before and i did went through very painful and difficult situations. If it happened before i met my protector, i would have sustained deep emotional damages in which would be difficult for me to recover from. With the protector, the same things happen or even they get worse, I lose friends, I get stressed, it gets painful, things go down, but at the end of the day i get stronger and I learn more from there. And the friends that I lose eventually i find out they are not beneficial at all and they get nowhere in my life and are in fact a very negative influence. I also quarreled quite a bit with my dad who has his own theories about Buddhism and he always tries to convince me to believe him, but somehow, after each argument he contemplated and he agreed and accepted my viewpoint a few weeks later! We also got closer after that. Things were also somewhat more difficult to achieve but when i did it felt very satisfying and i noticed i could do more after that. There were also things like gossips going around which made me think twice about doing volunteering in my center, but at the end I came to a conclusion that it was training to keep my motivation pure.
To me, this is the Dharma protector's blessing and assistance so that I can become a pure practitioner, and I really would love to thank him unconditionally for helping me. That was my experience with him when I think back, and I am glad he did because if I had not been exhorted to practice him, I would not have hold on to my Guru and Dharma center.