I think the items are a funny thing.
Is it surprising that each character in a given role builds similar items?
How would it be different if each character had totally unique items, but they ultimately gave the same end result?
Would you be more interested if any character could ultimately take any role? Want to start seeing BT and PD on morg? Rabadon's on Sivir? Not sure if that's better.
The real wrench in the gears are the unpopular items that people either don't get, get because they don't know what else to get, or get because they want to experiment.
Things like malady, nashor's tooth, stinger, Moonflair Spellblade, ect. People buying the 'wrong' items can totally break their game, if they would have otherwise done ok. I realize it's a learning experience, but the only way to stay competitive if you're new is to use a guide... and as a new person it may be a while before someone screams at your crazy build and tells you to find one.
I think the 'recommended items' are certainly a source of confusion or frustration for a lot of new people as well. With the exception of Morgana(or a select few others(out of 90+ champs), most 'recommended item' lists are ignored for the most part. Then why are they 'recommended'?
Of course, all this is moot for experienced players. They know what the items do, and the know what the best value for MR, Armour, AR Pen., ect is if they need to counter the other team.
Don't listen to me, I'm an idiot, but I think the game needs to lay out what items are likely to have a positive impact for each champ a little better, and maybe the ability to find a particular item a little easier. (Search box, like the one during champ bans?)
I think Viktor's item is interesting, but then he has 1 less inventory slot. Perhaps it should have multiple upgrades, to provide for more immediate incremental upgrades, but still retain the whole 'once you pick a path you're stuck' thing.
Aside from smart play, knowing when to get each item, and when it can provide the most benefit, is currently something that can only be learned from lots of reading, playing many many matches, and/or watching pro streamers for a while. The only way LoL will last more than a few years is to keep bringing in new players, and that won't happen if the barrier to entry is too high. I feel these sorts of considerations are important for ensuring the longevity of this game.
*shrug*
