@Barry Edgemon great question. I also love this "Pro Tip: long term or chronic unanswered questions lead to dysfunctional distraction, depression, frustration and confusion." To answer, when is enough enough? In the flesh it isn't. We all have a God sized hole we try to fill with stuff or substances or women and like all of Ecclesiastes states: it's all vanity, a vapor. I used to read Matthew 26:41 "Watch and pray so that you will not fall into temptation. The spirit is willing, but the flesh is weak.” and think oh the flesh is weak like it was a skinny little man trying to pick something up, but it's weak in every way. It folds to temptation, to comfort, to ease, to complacency. The flesh is weak in the way that it looks for the large, easy path not the road less traveled. I can know this and see it happen in myself all the time. In conversations with my wife, in how I discipline my kids, how I approach a problem client at work, how I respond to the Holy Spirits prompts, etc. I can know the pitfalls and yet still choose them because my flesh is weak. When I choose to follow the spirit, it's hard, uncomfortable, testing, it forces me to persevere, to push forward, and in the end is fulfilling and rewarding in a way I never knew. God is good, but he isn't safe or easy. God is wanting you to take the narrow less traveled path, but that isn't comfortable or simple and looks crazy to the world around you. When is enough enough? I think when you can readily listen and obey God's voice without a fight or a whining or a "oh man, cmon God, why that or why this person.". Peace beyond understanding is great, but obedience in faith is where the work is.