‘He’s afraid to upset her’: My friend, 78, has $500K saved and owns a home with his girlfriend of 20 years. Should he split his estate with his daughter?

Dear Quentin,

My friend “Bob” and I have been close friends for 40 years and I am the executor of his will. He is 78 and in declining health. Although not a college-educated professional, he worked very hard at a physically challenging job and was a diligent saver. 

Bob lives with his lady companion of 20 years in a house they purchased together, each contributing 50% of the purchase price and 50% of the taxes and upkeep. She is 68 and in good health, with a real-estate broker’s license and is a non-practicing…