It depends on the input impedace of your amp if a high impedance preamp gets a better sound out of the pickup.
I think if you play rather hard, the presence of a high impedance preamp helps more than when playing softer.
Higher piezo voltage needs higher current and that may break down the voltage (a bit more than usual) if the current couldn't be delivered by the piezo crystal, resulting in distortion of the waveform.
What I heard about the Fishman PP is, that is colours the sound and probably makes it sound less direct. I think a FDeck HPFpre would be better to find out if a preamp can help, since it is very neutral in sound (just 3 dB amplification for model I or II). Maybe you can borrow one to try it.
My Shadow SH-950 is rather thick (compared to the Underwood I have seen once). That means is would be hard to compare both, since for both you need to prepare your bridge differently. Putting a bunch of veneer to fit the Underwood into the Shadow wing distance might change the sound more than the real difference is and getting the same pressure would be hard to impossible as well.