Does It Really Matter If I Let My Tank Go Below ¼ Tank?

Yes, keeping your gas filled above ¼ tank extends the life of you fuel pump. It also keeps you from running out of gas and getting stranded.

The fuel pump normally generates a fair amount of heat as it operates, the fuel in the tank helps to keep the electric pump cool. Therefore running the vehicle with  very low level of gas in the tank does expose the pump to more heat than if it was with a higher level of gas. The fuel pump is unable to dissipate heat across the fuel. Heat does take a toll on most electrical components.

So why wait until the last possible moment, you are not going to spend more time in gas stations than if you do wait until it is almost empty.