How do certain "multi-hit" skills work?

[Naryoril]

just to say: it's not that hard to hit from behind with bootshine, or from the flank, even without any special skills or the like. For example bootshine: just run straight through the enemy and then use bootshine. There is a setting to automatically turn you towards the enemy when using a skill and it is activated by default. So you don't even have to turn yourself before using bootshine. Doing it like this you can hit an enemy pretty reliably from behind. you can do the same for flank hits, you don't need to turn towards the enemy before using the skill.

[gamepob]

just to say: it's not that hard to hit from behind with bootshine, or from the flank, even without any special skills or the like. For example bootshine: just run straight through the enemy and then use bootshine. There is a setting to automatically turn you towards the enemy when using a skill and it is activated by default. So you don't even have to turn yourself before using bootshine. Doing it like this you can hit an enemy pretty reliably from behind. you can do the same for flank hits, you don't need to turn towards the enemy before using the skill.

I have been doing just that and are somewhat successful in it. The problem is that my success in applying those added benefits in solo fight without CC-ing enemy, mostly depends on luck and not my own skills. Will I be lucky enough to actually get the hit I just made counted as hit or miss?
That's the main point here. Not "Can I do it?".