How could Jacob wrestle with God and lose? - God did not lose. He, evidently, chose to wrestle with him. Eventually He touched (struck) Jacob’s hip socket. Do you think that we can assume that Jacob limped from then on?
They wrestled all night? Why? Sounds like they physically wrestled. Why didn't they just talk? - Doesn’t it seem like God has to do something drastic to get our attention sometimes? Usually it takes something physical or our pocket books before we really listen to Him.
Was the other wrestler really God? - Jacob said, “For I have seen God face to face, - -.”
Why would the other wrestler cripple Jacob? Is there some point? - Jacob had been very cunning, with his brother and with his uncle. God had to show him that he needed to depend on Him in all of his endeavors, instead of his own physical ability or his clever cunning (thinking).
Are there hidden meanings or symbolisms here that an average guy is supposed to miss? - I would like to think that this example shows us that our natural abilities are simply gifts that God allows us to use to a certain point. John 15:5, “ - - for without Me, you can do nothing.” 2 Cor. 3:5, “Not that we are sufficient of ourselves to think of anything as being from ourselves, but our sufficiency is from God, - -.” He wants us to depend on Him in all things.
Why make this so hard to understand? - John 4:24, “God is Spirit, and those who worship Him MUST worship in spirit and truth (realty).” Read also John 3:3-6. - Praise the Lord!