Perhaps the Pirates are just trying to add some degree of difficulty to their year. Maybe working with the third lowest payroll in Major League Baseball is not enough of a challenge for them. The Pirates dug themselves a hole in April, going 9-16, to enter May with a 10-16 record (March opening days are weird). They've righted the ship, so to speak, in May with a 15-13 record to give a glimmer of hope that they can still make a run.
Their schedule heretofore has been brutal. Of the 54 games they have played, only 20 have been against teams with losing records. The combined record of the other teams they've played in those 34 games is 208-159, good for a .567 winning percentage. In those games, the Pirates have gone just 15-19, with most of the damage due to the old nemesis of the Milwaukee Brewers (2-8). The Pirates have fared better against the sub .500 teams (Cubs, Reds, Mets, Nationals), going 10-10 so far.
The good news is that better days lie ahead in June. Hopefully, unlike their namesake pirates of the seas, the call of better days does not cause a shipwreck against craggy rocks. In June, the Pirates play 27 games. Of those 27 games, 20 are against teams with a losing record currently. The seven games against winning teams are: the final game against the Dodgers in the current series, 3 on the road at Miami, and 3 at home against Milwaukee. As the records stand right now, the Pirates wouldn't play a winning team in the month of June after the 15th.
The split between home and road games is fairly even for the Pirates -- 13 on the road and 14 at home. So far this year, the Pirates have been abysmal on the road, so hopefully the lesser competition will start to build their confidence in that regard.
June 1st is far too early to start worrying about the playoffs. July is when a team will typically decide whether to fish or cut bait, ahead of the July 31st trade deadline, but you also can't allow yourself to get too far under water. The first thing the Pirates need to do is get back to .500; no team makes the playoffs under .500. In recent years, 89 wins has been the magic number to secure a playoff spot. The Pirates would have to go on a tear to achieve that, but maybe they won't have to this year.
If you set aside the current division leaders of Milwaukee, Atlanta, and San Francisco, there are no other teams really putting up strong records yet. The Cardinals are 3 games over .500. The Marlins, who are a prime candidate to swoon in the summer, are just 2 games over. The Dodgers are spinning their wheels and just 2 games over. The Rockies are already scheduling their return trip to Earth and 2 games above the break-even mark.
It's looking to me like maybe 86 wins could be enough to sneak into the 2nd Wild Card slot this year. For the Pirates to do that, they would have to go 61-47 in their final 108 games (.564 winning percentage), which is essentially the Atlanta Braves current winning percentage. Last year, when they went 94-68, the Pirates had a .580 winning percentage, so it's definitely in their wheelhouse to pull off.
So do not abandon all hope ye who enter. At least until July 1st. Aaargh.