Mate I know where you are coming from honestly.
But I think you need to step away a little, stop over analyzing it and take a little time out, just for yourself.
Turn it all off for a weekend or even a week. Get out in the bush and go camping for a weekend, go get shitfaced and laid, enter a mosh pit or something, Climb a mountain, plant a garden, lay on a beach and count different coloured pebbles.
Basically just get a reset in your head and soul, all this shit eats away at who you really are, not just to you yourself but all those around as well.
I have been in the position of not having to worry about money, yeah it does take a load off. BUT, it does not make one iota of difference in the rest of your life at all. You still have all the rest of your life to consider as well, the bills might be gone but none of the rest of it is.
You are still the same person , but you can pay your bills and afford some extras, So What ?
The stress of everyday life does not leave, it doesn't make dealing with it any easier either, if anything it can become more complicated as you are dealing with managing not only the wealth, but also the affect that has on those around you, friends and family, loved ones and business partners as well.
You have said it above yourself, you have compromised yourself , who you are in order to achieve wealth , you don't need to remove the emotion you need to embrace it along the way otherwise you will lose yourself in the process of trying to achieve wealth.
"It is likely that I have compromised my value system in many, ways and also been less than charitable in many situations I could have given a little more. What has forced me into acting in ways that if I observed from afar, I would not want to associate with myself?"
I personally don't see wealth measured in Dollar signs any more, it took me a while to get to that point as well. But I measure Wealth in happiness, Family Friends, laughter, fun, enjoyment first and Dollars a very poor second.
Money will buy you very few of the above, and if you sacrifice those that it wont buy for those that it will, then you are all the much poorer anyway in my mind.
RE: Getting lucky - 777