Yeah, there is a big strategy part to the system so it's almost essential for captains to prepare for this ahead of time imo. They have to fill to 5 man rosters and get 1 sub minimum, so they really have to conserve money in a smart way while at the same time form a team they want; while thinking about all the other captains, their money, who they might go for, etc.
But in reference to that example ^ spending all your money on 3 really good players you just can't do w/o being screwed. For starters, you have to have at least 6 on your roster so there's that. You have money to get good players, but you may have to buy some cheaper players to save money and average out money per player to what you can afford.