Charge time is the most important issue when it comes to any kind of trip. Assume your 300 mile range car (270 usable). There is a significant amount of planning required to find chargers along the route compared to zero planning for a gas car trip. Even a 3 hour drive for the weekend at the beach might involve some sacrifices (can I run AC the whole way or do I have to stop and get a quick charge?). Then you have to plan out where to recharge for the return trip which might not be convenient to where you are staying. (and do it all over again on the way back)
For those taking road trips that involve planned charge stops while gas cars can stop just about anywhere without planning. You can stop when it is convenient for the people rather than for the charging. And there is the issue that you can't fast charge past 80% so you effectively operate with 60% of the range when on trips (don't run down below 20% and don't charge past 80%) so that 300 mile range car is having to stop every 180 miles for juice.
"When I drive my hybrid and the gas is getting low, I begin to stress out because if I am somewhere unfamiliar I don't want to drive around trying to find a gas station."
Never had this problem with my hybrid. Gas stations are everywhere, most people don't run down to E before thinking about it and you can always top off anytime you pass a gas station.
"I remember when I was in college, being super stressed out, because we were driving back at 2am on E, with most of the Gas Stations being closed."
I have driven all night many times, unless you are in the middle of nowhere, gas stations are frequently open 24/7 (you pay at the pump these days). Truckers do this all the time. This is another case where almost no planning is really needed if you plan to make a long trip all night in a gas car.
Eventually, chargers will get to the point that they are everywhere but we are still a ways from that. As it is now, a long trip in an EV offers challenges and stress that gas cars don't have to deal with.