Does being STO make you a loser in the eyes of this world? How do you cope?

[flow]

...Do STS-entities really feel empty?

rich and "succesful" are not at all necessarily STS beings. for the most parts they are victims of STS beings, who direct this game.

...Since the path is fully embraced and chosen I imagine that they must feel satisfaction in domination over others-selves. I believe they are tempted by the raw power that awaits. The path towards that is hatred.
I think it's the feeling of emptiness only for those entities who are confused aka those stuck in the sinkhole of indifference.

i'd say that is correct, at least i feel the same.

How does one know where one is in terms of spiritual development? Negative or positive?
I must admit myself, I'm constantly between the two I don't know who I really am. Can anyone help?

STS beings feel they see a glimpse of true nature of things which brings about a sense of meaning and a bigger picture, a wisdom of some sort, just like STO ones do. both STS and STO beings want to share that wisdom with others. but then, if STS being see that others around it are not really responding to their attempts to describe what they see as ultimate truth, in the eyes of STS being they are looked like stupid, ignorant fools who must be subdued to the wisdom of STS being for their own good, since they themselves cannot find a way to awakening. so, beginning STS steps may look like a STO things to the amateur STS being. it is later, by consciously using control and manipulation, it takes taste in power over others and being cunning and wise and became consciously STS.

STO being also wants to help its brothers and sisters to become awaken, but only offers help and try to act upon requests. STO being try to make itself better, so it shines brighter with its open heart and thereby welcome others to address their issues and worries, so it can serve them.