Planning

I'm a total failure at logistics and finance, hence the utmost stress when planning for a trip. After all the energy and time expended, I somehow almost always ended up with the more expensive options, even though I always started with the goal of finding nice yet value for money lodging, flights, etc. 

I think you need to be an expert at math and logic, be meticulous and at the same time creative and resourceful in order to plan a perfect trip. Honestly I feel the best way is to not have options and not to compare. Then there's less of the beating yourself up and undue stress of making a bad choice. Studies do show that having more choices actually make one unhappier and stressed but a healthy dose of say 2-3 options make for a better emotional state.

Speaking of emotions, I don't know why I actually teared at BS. It surprised even myself and I was merely recounting some minor unpleasantries I encountered with someone I don't really care about or am close with. Do not like being overly emotional at all.