If a permanent has multiple instances of cumulative upkeep, each triggers separately. However, the age counters are not connected to any particular ability; each cumulative upkeep ability will count the total number of age counters on the permanent at the time that ability resolves.

If a creature returned to the battlefield with Dreams of the Dead would leave the battlefield for any reason, it’s exiled instead — unless the spell or ability that’s causing the creature to leave the battlefield is actually trying to exile it! In that case, it succeeds at exiling it. If it later returns the creature card to the battlefield (as Oblivion Ring or Flickerwisp might, for example), the creature card will return to the battlefield as a new object with no relation to its previous existence.

This is a replacement effect.