What you should be looking for here is to play familiars to curse your opponent's deck, use apothecaries to draw copper and leave curses/estates on top of your deck, and cleverly use a lookout to trash those bad cards. Once you can do that you can then create an economy and do fancy things with extra golems and council rooms and outpost. Any turn where you trash a copper and buy a silver is essentially wasted since you lose economy, drawing power, and deck control from the apothecaries. The second lookout and island therefore gave no economy and very little long term benefit.