[asauce]

It does depend on the situation, and how easily you are able to change tools down the road. However analysis paralysis can be a never ending cycle, so at a certain point you need to accept that you just need to pick one.

If its a low cost, easy to switch tool then I'll force myself to stop over analyzing and just dive into the tool. Theres no better way to learn a tools shortcomings than actually using it.

A high cost tool is a lot more difficult. Personally, I assign myself a deadline to pick the tool (eg this week I'll research, next Monday I'll purchase) and then I must follow through on that day. Otherwise I will just keep overanalyzing every single comparison until neither tool looks attractive.

There are situations where you are going to pick the wrong tool. It happens. An example is I started music production in Logic Pro X, hated it, and ended up switching to Ableton. I spent a lot of time researching the two, but it was only once I started using them that I realized which tool suited me better.