Put the top two cards of target player's library into that player's graveyard. If both cards share a color, repeat this process.
If Darksteel Colossus would be put into a graveyard from anywhere, reveal Darksteel Colossus and shuffle it into its owner's library instead.
Grindstone mills 2 cards at the same time, and Darksteel Colossus's ability is static, not triggered, and creates a replacement effect.
So the simplest of these questions to cover is that of Yixlid Jailer. The Colossuses never are in the graveyard, so Jailer's ability will never affect them.
Since Grindstone mills 2 cards at the same time, you will see both and move both at the same time, so if one is a DSC, the other will still be milled before the DSC gets shuffled in. The shuffling in replaces the put into graveyard though, so they will get shuffled in before you repeat the process. So if you have 2 or more DSCs (or Serra Avatars or Legacy Weapons) in your library, the result will be an infinite loop with no optional actions for either player meaning the game ends in a draw.
If there is a single DSC/Avatar/Weapon in the library then eventually you will reach the point where that is the only card left in the library. You will have Grindstone telling you to mill 2 cards, but with only 1 card will do as much as possible, milling that one card. Since there is no second card, there's no possibility of sharing a color, so the one card gets shuffled back in, and the process does NOT get repeated, leaving you with just the one card in your library.
And just to verify, you don't mill them one at a time, correct? So, you can't mill the same DSC twice if it's the last card in your graveyard?
I'm thinking of dredge and bazaar, where draws are done 1 at a time.
If an effect tells you to "Draw X cards," you treat it as X separate instances of "Draw a card." This is specific to drawing cards only, and doesn't apply to other actions
As for effects like that of Leyline of the Void, Grindstone does not care where the cards actually end up, just whether or not the 2 cards share a color.
Scarecrow does bring up a lot of interesting questions, like if Glittering Wish allows you to choose Lightning Bolt from outside the game. I would say yes, based off the definition of Mulitcolored in the glossary of the comprehensive rules:
Painter's Servant does not interact with sideboards at all. The sideboard is outside the game completely, so a Painter's Servant will not change what you can get with Glittering Wish.