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There's a huge philosophical question:  when a talented player runs into a holdup, do you try something else or do you see whether you can build on the learning time you've invested?
James made a number of fascinating points about this, which pretty much line up with your observations point-by-point.  He's got some data, so maybe with next post we can kick the soccer ball down the field on that some.
First question you've got, is WHO precisely replaces the talent that you're bailing on.  Where you're undecided, where it's at all unclear, it's better to resist the knee-jerk impulse to flush the guy you've spent your time on.  But if there's any doubt at all, you want to take advantage of your investment.  In the cases of Ackley and Smoak, the "threat" of roto bustouts is completely realistic.
Smoak and Ackley, as you note, are making it that much tougher to bail on them because they AREN'T inflicting a huge cost on the inquiry.  A very even-handed survey, this...