I would not be able to break even with an S9 within the first year. According to that, even after 360 days, I would still be $1999 in the red.
The calculator assumes an increase of 5% in the difficulty every 14 days, so that's not necessarily reflective of what could actually happen. The difficulty gets adjusted based on the network's total hash rate, so if miners pull out (stop mining for some reason) then the difficulty increase won't be as big as it might have otherwise been. Here's a chart of historical difficulty - you can see there were some dips:
https://bitinfocharts.com/comparison/bitcoin-difficulty.htmlThe calculator also doesn't consider changes in the exchange rate - if the price of bitcoin goes up again this year that'll make your miner more profitable.