Thanks for checking! Yeah, I forgot that you can't use Innovation on Villa after returning to your Action phase, because Villa has then put itself in your hand.
I think this would work as intended with Sheepdog and the +$1 token on the Sheepdog pile:
You have a Wine Merchant on your Tavern mat. You have $1 at start of Buy-phase. You use Woodworker's Guild to gain Villa, returning you to your Action phase and ending your Buy phase. You play Sheepdog because you gained Villa, giving +$1 from the token. Can you now discard the Wine Merchant? Probably not.
Still same as before--you can discard Wine Merchant. Again, at least online, it looks like this is because the "when gain" triggers are happening before Villa returns you to your action phase. scolapasta, I tried both with Villa first and Sheepdog first, and at least online, I can discard Wine Merchant both times. I bolded the rows where the +1 action from Villa's below the line text is kicking in.
Reacting with Villa first:
Turn 18 - Wizard_Amul
W starts their turn.
W gets +$1. (Key)
W begins their buy phase.
W trashes a Hunting Lodge.
W spends 1 Favor.
W gains a Villa.
W puts a Villa into their hand.
W gets +1 Action. W reacts with a Sheepdog.
W plays a Sheepdog.
W gets +1 Coin (from Teacher).
W draws a Teacher and a Hunting Lodge.
W ends their buy phase.
W discards a Wine Merchant.
W plays a Hunting Lodge.
W draws a Villa.
W gets +2 Actions.
W plays a Teacher.
W puts a Teacher on their Tavern mat.
W begins their buy phase.
W buys and gains a Peasant.
W shuffles their deck.
W draws 2 Villas, a Sheepdog, and 2 Hunting Lodges.
Reacting with Sheepdog first:
Turn 18 - Wizard_Amul
W starts their turn.
W gets +$1. (Key)
W begins their buy phase.
W trashes a Hunting Lodge.
W spends 1 Favor.
W gains a Villa.
W reacts with a Sheepdog.
W plays a Sheepdog.
W gets +1 Coin (from Teacher).
W draws a Teacher and a Hunting Lodge.
W puts a Villa into their hand.
W gets +1 Action.W ends their buy phase.
W discards a Wine Merchant.
W plays a Teacher.
W puts a Teacher on their Tavern mat.
W begins their buy phase.
W buys and gains a Peasant.
W shuffles their deck.
W draws 2 Villas, 2 Hunting Lodges, and a Contract.