hiccup,
There is not much more I can add that hasn't already been said.
I was raised as a JW and left (physically anyway) as soon as I turned 18. I was in the top 1/4 of my high school class academically. But because the Society discouraged higher education, my parents did not encourage me to look at colleges and because I was still psychologically and emotionally held in check by the religion, I did not pursue it on my own either.
Because they believe that "the end of this system of things" will come "like a thief in the night", any investment in this life is considered mostly a waste. One is really expected to spend only enough time and attention on secular work to get by, spending the rest (ideally the majority) of one's time in the service.
Here is, I think, the core contradiction:
Matt. 19:24 "it is easier for a camel to go through the eye of a needle than for a rich man to enter the kingdom of God." (NIV)
Luke 17:20-21 "Once, having been asked by the Pharisees when the kingdom of God would come, Jesus replied, "The kingdom of God does not come with your careful observation, nor will people say, 'Here it is,' or 'There it is,' because the kingdom of God is within you." (NIV)
I think the first might be an exaggeration. After all, wasn't Job given many riches? And wasn't King Solomon, besides supposedly the wisest man on earth (and a magician as well), also filthy stinking rich due to God's blessings. (Having asked God for wisdom rather than material wealth, God gave him both.)
I suppose they had both already passed the camel litmus test.
If your father has become seriously involved with the JWs, there is not really much you can do at the time. Anything you say that challenges the religion will brand you as pawn, however innocently, of Satan. It often takes many, many years for the veil to fall from before a JWs eyes. And often, even then, so entrenched will they be that they will stick with it rather than lose connection with so many loved ones.
I went through many, many years of emotional and psychological turmoil after I left. There are still today, nearly fifteen years later, remnants of the teachings lingering around in the most unexpected places.
I'm sorry to have to say this. And it's tough medicine. But if he's already this entrenched, be prepared to lose touch with him. Not that you shouldn't try though.
Have a heartfelt talk with him. Explain that you're not trying to turn him from the religion. But explain that if "the end" is to come, no one knows when it will. And it does more harm than good to cause life in this world to be so difficult. Greed is one thing, but there is nothing wrong with providing yourself and your family a comfortable life. There must be a balance.
Sincerely good luck hiccup.