If you meet the contract goal at any point during the contract you will get credit for it. I think the goals are too much though. If you start a Phillies franchise with real contracts, your contract goal is to win the division series by end of year 3. With the roster the Phillies have, not losing 100 games in a season would be a more realistic goal than that.
The goals seem to be focused on budget size which is true to a certain extent but they should be proportionally based on not only budget but also age of team (average age of 25-man roster), skill level (average rating of 40 man roster), and farm system (average potential of all players not on the 40 man). That way your goals would be more realistic to your your current team position. Since I can assure you no one in Philly is thinking the Phils will be back in the post season until Mike Trout signs with us in 6 years.