The way the loot and light level works is disgusting. If I have 3 warlocks and I've beaten hard mode 6 times, then why should someone with 1 Titan be a higher light level than me? Is it because they are just luckier? Luck should have nothing to do with my rewards. I've completed the normal raid around 18 times and the hard 6. I have yet to receive a helmet at all. Getting max light isn't even a testament of skill or time played. It's strictly who's luckier. The loot should work as follows.
1.) killing a boss should yield a guaranteed item
If the light level is going to remain random then I should at least know I have a piece coming to me whether it's a duplicate or not.
2.) any duplicate pieces should only have a chance to be rolled higher than the already earned or equipped piece.
If I have a 314 kingslayer shell and pick up another, it should only have a chance to be 315- 320 and so on until I reach maximum possible.
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I believe your point 2 was the way this "smart loot" was supposed to work. At least that's what most assumed based on Bungie's description in the pre-launch videos. Something similar to, "The game will take into account what you currently have equipped when deciding loot". I'm paraphrasing and going from memory. I'm going to go back and take a look at the vids.
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It may be slightly easier if you have 3 of the same classes as you can swap gear around but in my case, I can only run it once a week as only one of my characters is the right level. Then I run it only to find out I get nothing.