Your right on all counts. Your mother must have had a very strong father where I don't think that Madonna did. My grandmother lost her father at around 5 and she was a complete mess. My poor mother...Your right was all have lessons in life and tragedies, but sometimes it affects other differently. Honestly, I really don't have any real feelings for Madonna because I don't know her at all.
You're both over-thinking her.
She wanted to be "rich and famous" and through force of will, smart business dealings and a semi-astute eye for population culture she got both.
Yes, she's one of the most successful women in pop culture managing a business worth a couple hundred million. And yes, she's lacking in any real talent. Prince,a guy with genuine talent, famously walked out on one of her shows because he was so offended.