yes, you guys aren't making this too difficult. Sharp friend only cares about getting the best of the number. In the end, he figures the results will take care of themselves. He only cares that he's getting the best price.
GW, your "good" and "bad" bet tracker is something similar to what I used to do, but in the end it's just too much work for me to sit there and decide whether I made a proper or improper bet. If I am getting the best of a number on something I feel strongly about, I'll try to bet it and not think too hard about whether I should or not. An easy way for me to get by doing that is by putting in a price in the exchange. Sometimes they won't match me, and I'll have to decide later whether it's worth a couple of extra pennies to go match someone else or to leave it be.
the "right side" argument we could all have until we're blue in the face. I had a discussion with Ron Sacco about six years ago about "right sides". He told me "Son, I've been doing this for 50 years, and the only right side is the one who gets the money after the game" or something to that effect. I wanted to pop him across the forehead for his condescending attitude. Some people feel that way, but most I run into are like me if they watch the games, want to learn for future references, etc., what the "right" sides are, regardless of who gets the cash in one specific game.