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The problem with Pittsburgh is that they draft horribly and they sign a bunch of average veterans every year to play around their crappy prospects. They probably had a few bad drafts in the 90s and the team became less and less appealing to play for. They're a small market team and as the best prospects became unsignable, Pittsburgh has been left with some shit drafts, and only average players will sign with them.
A team like Tampa, Florida or Oakland spends their money scouting and developing players. That's why they're successful. You rarely see those teams sign a big money player (except when the Marlins go crazy every 7 years and then dismantle). Not that Pittsburgh has signed any big money guy in a number of years but they end up blowing big chunks of cash on a bunch of mediocre, replacement level guys every year (the Royals are also infamous for this.) If you're going to suck, why not suck for the league minimum and give the young guys a shot?
Also, the Jason Kendall contract killed them a bit.
There seems to be some rays of hope with Pedro Alvarez, Jose Tabata and Andrew McCutchen though. Oh and Brad Lincoln. Maybe things will turn around in the next few years.
Baltimore is a bigger problem. No one wants to play there because the Yankees and Red Sox will always be on top. Tampa has established themselves as a model franchise and they'll be a winner for a while as well, and Toronto always manages to field an ok to decent team as well. It's too competitive. They have money, but no free agents want to sign there and no top prospects want to sign there when they're drafted.
The Nats are going to be fun to watch in a couple of years. They're the next Tampa I'd say.
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