The stipulation is that sometime after the start of turn, you have 5 cards in hand, then draw everything else by playing 2 cards. It says nothing about any previous cards that brought you to that 5 card state, or about other cards in play.
9 Fishing Villages in play from last turn.
-Play Chancellor, discarding deck.
-Play University, gaining an Inn, shuffling all Actions in my discard into my deck.
-Play Jack of all Trades, drawing back up to 5, and emptying the Silver pile.
--------------------(now at point where puzzle starts)-----------------------
-Play Scrying Pool, drawing deck.
-Play Madman, drawing everything else.
Well, you've got 92 Actions in your deck(if you're only playing 10 card piles), of which you're playing 14, with 78 left over. So your max hand size for Madman is 79. But there's 59 Copper, 39 Silver, 29 Gold, 13 Potion, 21 Victory cards, and 9 Curses left, for a total of 170 cards you have to draw(minus one you got from Scrying Pool). So you need some more stipulations on the cards you have i.e. you need piles bigger than 10.
Also, to fulfill the puzzle, you need to have something to gain from the trash(Rogue/Graverobber), otherwise you don't have the Hermit you trashed to get Madman and your deck does not have maximal size.
Probably need Rats, Young Witch, Page, and Peasant(adding 10, 10, 20, 20 cards). Also having Ruins would help. You also can get more Madmen for even more Action cards.
This only leaves 4 more Kingdom card slots, so you have to pick and choose the remaining ones. Rats, Page, Young Witch, and Peasant bane fill out all but the last slot, and don't cover the difference.
I don't think it's possible to get any more without the help of Black Market, with the rest of the Action cards not in the Supply. That should definitely cover the difference, and it frees up slots you only play one of, all the cards in your 5 card hand. So you can take Port, Urchin, Tournament, etc. and make it up to drawing your whole deck.