Just as a matter of interest, what benefits would a Polish passport have over your American one?
Quite a lot - unlimited stays in the EU, no need for a work permit, etc.
(but never joins military which apparently keeps him from losing citizenship in Poland)
Automatically stripped of Polish citizenship at this point.
-Grandmother born in 1932 in US
Automatically US citizen, which would result in Polish citizenship being awarded and then stripped due to the law in place at the time.
-Father born in 1958
Wouldn't have had Polish citizenship to begin with - and would have been stripped regardless by the 1951 law.
According to some
Ignore all these reports and look at the law. She was born a US citizen, which meant she automatically lost Polish citizenship. If you consider that at the exact moment of birth, she would have been a Polish and US citizen - but Polish law would have stripped her of the Polish citizenship at the exact same moment. The rest is irrelevant. There's no provision in the relevant law for being born abroad - the US is and was fairly uncommon for awarding citizenship based on jus soli.
help me sort this out
As it stands with the law, you have no chance. Polish citizenship passes down from parents to children and can't skip generations - but at least 3 generations would have been stripped of any potential citizenship.
Your best hope is to find a lawyer who is well connected - but in all honesty, it would be better to simply move somewhere with easy citizenship laws (Belgium for instance) rather than spending a lot of money trying to chase something that you're likely not entitled to.
Also I hear that the laws are somewhat subjective so I hope that being an educated and productive member of society would help
No. Polish law simply doesn't work like that - you're either eligible or you're not. They must make decisions in accordance with the relevant law - your only hope is to find someone that's 'connected' to find a way to issue a favourable decision. However, in your case, I just cannot see how you'd be eligible - bearing in mind that your grandmother AND your father would have to claim Polish citizenship first. You can't 'jump' generations.