Alduro,
Having owned all three pistols you mention, here are my observations:
If the SIG 229 just fits your hand, the 239 may likely be too small. It has a slightly shorter and noticeably thinner grip.
The PCR, on the other hand, is just a shade smaller and lighter overall than the 229 and virtually the same size as the 239, but its grip size is comparable to the 229's. I would guess that if a 229 fits your hand, so will the PCR.
The 239's frame is thinner than the PCR's by just a whisker. And it's no lightweight either. The 239 is heavier than you might think.
Although my 9mm 239 is an excellent shooter, I prefer my PCR when it comes to concealed carry. With flush-fit 14rd mags, I'm gaining an extra six rounds without a comensurate gain in size or weight.
In my opinion, where the 239 really shines is in .40s&w or .357sig. Its power to weight ratio makes good sense in these calibers. The pistol is small enough to conceal, yet it's not unpleasurable to shoot (as is the case with some small frame / large caliber handguns).
And as for your SIG 220, I don't think most SIG-o-philes put any extra premium on its value due to its Cold War production status (unless you're saying your particular pistol has some unique Cold War significance -- in which case, it may indeed have collector value). They put an extra premium on it because it's arguably the best box-stock .45 combat pistol.
Take care. Marko