Slade, this is my humble opinion - not that you asked...but...
I think that the 'real' you needs to come out now. When you were making all of that money, it was hard to see that difficult times were coming. Hindsight is 20-20, and we all could have learned to set more $ back for our kids, in times of trouble, instead of driving the latest car, and having a huge home (filled with uneeded crap). No one needs that much space or stuff.
That being said, I think you are a good dad that really loves his child, and you're not getting a fair shake.
Gretchen just doesn't seem to be 'the one' for you.She's way too independant and opinionated (which isn't a bad thing! but she's too much for you, and it depresses you).
You need someone who is sweet, kind, and not so ...elevated. Just a down-to-earth girl, who is good to your son, and can be a partner in your life, someone that will help you through the hard times, and vice versa.
Slade, you want someone to walk side by side with you through this life...not 3 feet in front, and you don't want someone who is 3 feet behind that you control.
Shake off the 'rich boy' shackles, the ego, and stand up! Become the caring man that is just behind that facade - you can do it right now. Good luck and Godspeed!