There are a few 'one or the other' questlines where there's a decision you make that forks the quest and you end up with one of two possible rewards and can't get both. The only two that I can think of off the top of my head are Azura's Star (Both rewards are similar enough anyway) and the Dark Brotherhood questline.
If you don't want spoilers I'd suggest saving your game before starting the quests and playing them through twice continuing the file with the item you greater desire.
I personally wipe out the dark brotherhood any chance I get in any incarnation of the Elder Scrolls and I'm just fine with those results. I know I'm the minority there though.
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