This sounds very familiar. For example, the simple task of buying a computer from parts could easily take me anywhere between one to six weeks. And this is aft

This sounds very familiar. For example, the simple task of buying a computer from parts could easily take me anywhere between one to six weeks. And this is after the months it took me to move from the desire to upgrade to a commitment. Similarly, for upgrading my laptop, I have on more than one occasion waited for newer models to be announced or become available, only to finally pick a different one. There are some things which helped me deal with this tendency to over-analyze such decisions: 1. Accept that this is who you are. Even though it feel as time lost, or spent unproductively, you are still benefiting from it. For me, though it still annoys me, doing the research is also a hobby. 2. You are requesting a tool for rational decision making in the title. But I doubt that is what you need or want, or even if such a tool would actually be helpful. For example, what you could do is write down all requirements, give them a weight and scoring and fill in some type of a matrix. If you are similar to me, you'd likely spend even more time analyzing, tweaking your weights, assigning your scores, etc. 3. Realize that the perfect decision does not exist. And no amount of analyzing will prevent that. Often though, making a 'bad' decision will either have a minimal impact on your life, or, can be easily corrected (return policy / low price compared to disposable income). Learn the difference between those types of decisions. 4. Delegate some decision making. For example, when I am looking for a new car, I'll call one of my friends whose opinion I trust implicitly. I hope this helps