I use a card that allows me to trash 2 cards from my hand (like Chapel). I trash Market Square and another card. Are the cards trashed simultaneously or sequentially? Does either possibility allow me to use Market Square's effect? If so, where does the Market Square end up?
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The cards are trashed at the same time, so if you are trashing Market Square, you would not be allowed to discard Market Square for its effect also.
Also, from the Dark Ages rulebook:
You can't gain a gold by trashing Market Square, only by discarding it. Once you've trashed it you can't then discard it. Consequently you can't gain a gold by using Chapel to trash it and another card.
The only way I can see to trash the Market Square and use its ability is by discarding it, reshuffling, picking it up again and then trashing it. This could be done using the Doctor with a bit of luck (or a very small deck):