Checked again; play2draw's solution actually works in the case where you go first without Great Hall. Here's the worst-case scenario (I stopped when the pin is complete at the end of turn 11; getting yourself set up to pick up VPs works the same as before):
1 - 4c1e - buy IW
2 - 3c2e - buy Chapel
(reshuffle)
3 - 3e2c - do nothing
4 - 5c - buy Village
DISCARD = Village, 7c3e; DECK = Chapel, IW
(draw IW, Chapel, reshuffle)
5 - Chapel, IW, 3c - IW (Island, draw 1c), chapel 4c
6 - village, 1c3e - village (reshuffle, draw 1c)
DISCARD = Village, 2c3e; DECK = IW, Island, Chapel, 1c
7 - Chapel, Island, IW, 1c1e - IW (Village), Chapel (1c1e)
DISCARD = Chapel, Island, IW; DECK = Village, Village, 2c2e
8 - Village, 2c2e - Village (draw Village), Village (draw Island)
DISCARD = Village, Village, Island, 2c2e; DECK = Chapel, IW
9 - Chapel, IW, Island, Village, Village - Village (draw 1c), Village (draw 1c), Chapel (2c)
DISCARD = Chapel, IW, Island, Village, Village; DECK = 2e
10 - IW, Village, Island, 2e - Village (draw Chapel), Chapel (2e), IW (Militia)
DISCARD = IW, Village, Island, Chapel; DECK = Village, Militia
11 - Village, Militia, Chapel, Island, IW - IW (Masquerade), Village (draw Village), Village (draw Masquerade), Island (Chapel), Militia, Masquerade (nothing to draw, nothing to pass, trash incoming card)
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For the case where the Chancellor player goes first, the solution I posted above works (pin complete at the end of turn 10).
*edit* Actually, I'm wrong. The solution from my previous post doesn't quite work, because of the VP stuff at the end.
Specifically, once you IW yourself a second Island, it becomes possible to draw (IW, Militia, Monument, Masquerade, Island) on any given turn. With that hand, you can IW yourself a Great Hall to make it possible to draw your entire deck and continue the pin, but doing so makes it impossible to Island away your IW (since it's in play).
However, the addition of Peddler to the kingdom makes the solution work. Play the same game up through completing the pin on turn 10. On turn 11, instead of IW (Monument), you IW (Peddler). You do this four times, on turns 11-14 (you are guaranteed to be able to play your entire deck on these turns, so Peddler will always cost $0). Then you IW (Island) on turn 15. On 16, your turn is:
IW, Militia, Masquerade, Island, Great Hall - Great Hall (draw Great Hall), Great Hall (draw Village), Village (draw Village), Village (draw Peddler), Peddler (draw Peddler), Peddler (draw Peddler), Peddler (draw Peddler), Peddler (nothing to draw), Island (IW), Militia, Masquerade (nothing to draw, nothing to pass, trash incoming card), buy Monument
Your deck now consists of (Masquerade, Militia, Monument, Great Hall x2, Village x2, Peddler x4). With only 3 terminals, you are guaranteed to be able to play your entire deck without gaining any cards every turn. You can even pick up a second Monument to double your VP income rate without risking letting up the pin.
With that revision, the Kingdom becomes (Chapel, Chancellor, Village, Great Hall, Masquerade, Ironworks, Militia, Island, Monument, Peddler) for a total of 10 cards - just fits!