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Because this has too much text for one card, I have now broken it up as so.

Mighty

Sorcery
~ cannot be cast before your 6th turn, be countered or played by a player more than once per game.
If your life is less than 20 it becomes 20. You lose all poison counters. Shuffle your graveyard and all exiled cards you own into your library.
Search your sideboard for Quester and put it into play.
Exile ~.

Quester
Artifact
Shroud
Only Mighty may put this card into play.
You may discard at most 5 cards, and lose at most 3 life each turn. You cannot gain life or prevent damage, your creatures cannot attack or block.
When you level up a creature put a mighty counter on ~.
When you complete a quest put 5 mighty counters on ~.
If ~ has 20 or more mighty counters, you win the game.

There is still a lot of text but I've made it more manageable.

There becomes lots of interaction with the player and the cards they play to stop them winning, I feel the card is undermined if it can be removed. Although good point with greeny.

How much progression would you assign for quests vs leveling Kingreaper?

I've adjusted it to make leveling harder against questing, leveling is indeed a bit easy and less interesting.

This is the most ambitious card I've ever designed.

lol