Damn. The timing. fistbumps back.
Guilt is a useful thing. Having an overly sensitive guilt function can be debilitating. I think your situation is a little tougher because you have more fun money. Granted... I was essentially just gifted a house. Out of a taxpayer funded subsidy program. That came about because of the '08 crisis. Caused in part (I'm guessing) by Morgan Stanley.
What would winning guilt free look like? There's hardly such a thing as totally independent bootstrap-pulling. There's just the suburbs where you're aren't daily reminded of the slow decay of Western society.