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... but it's interesting to hear you so sky-high on him.  Maybe I need to revisit.
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My complaints are in the context of Upton vs (say) Adrian Gonzalez, not in the context of Upton vs Michael Saunders or Matt Tuiasosopo...
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1.  BJ Upton had a super early HOF season and then has followed up terribly, in Ruben Sierra fashion.  I fret about Justin Upton having a lousy trajectory on his career arc.
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2.  Another potential crash involves the Eric Davis path to 110 games a year.  Both are super tightly-strung track type athletes.  Justin Upton's already got a labrum at age 23.
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3.  Upton doesn't have the EYE that greatly raises my comfort level when you're talking 9 digits on a player's contract.  He's been at 0.40 since he hit the majors.
I'd have been comfortable talking Pineda for Adrian Gonzalez if he agreed to a contract extension.
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4.  And you've got to negotiate a deal with him the same week you trade for him, right?  It's not like he's signed below market, like Felix is.
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4.  Neither is Upton a position-scarcity guy you can easily fill in the Rich Poythresses around.  Cf. Zimmerman, Hanley Ramirez, Longoria, Robison Cano etc.
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Upton is certainly going to be a Jay Buhner-level player, but there are guys like Heyward, Zimmerman, Votto, Hanley Ramirez, Longoria, Jay Bruce, and Ryan Braun I'd be far more comfortable targeting in a Pineda deal. 
Still, I'd cheerfully acknowledge the argument involved, if somebody thought Upton were going to the HOF.
And, of course, it's not like you're going to trade for a .300/.400/.500 shortstop who is signed below market value, so yeah.  And Upton's the one who's available, not Evan Longoria.