Doing the math, even in the worst circumstances (very cold or very hot temperatures) with a 300 mile range battery that you max out at 80% charge and avoid going below 10% charge, I can get back the majority of my commute and even have enough charge to go into the city over 50 miles away on the weekend. I would only need to stop at a level 2 charger every other week or so. 2 weeks if I don’t need to go to the city. My work is nearby a level 2 charger and places in the city even have level 3 charging. And that is worst case scenario getting only 2 miles an hour off a standard wall outlet as opposed to the optimum 4 or 5 miles.

I feel far more confident about battery range. The 3-4 trips that are more than 250 miles round trip a year are fine if you plan the route and are okay stopping for half an hour. With kids and a dog a stop in a ICE vehicle could easily take that long anyway.

I think this depends too much on your car and how you use it to make generalizations like "is usually overkill".

With an 11kW charger and assuming 12h in the garage, I can charge 132kWh in a day, which is far more energy than my battery can store. Thanks to this, when I park my car and decide whether to plug it in, all I need to think about is whether the car has enough charge now for my needs tomorrow. If it does, I leave it. If it doesn't, I plug it in.

With a 1.8kW charger, I'd only get 21.6kWh overnight. In my car, this is ~100km of range (~60mi) and about 30% of the battery. Now I either need to charge it every day (and add the hassle of unplugging/plugging every time I use the car) or I need to think about it more.

It's a matter of individual preference whether it's worth a few hundred dollars to avoid that friction but to me it's more than worth it for something that's part of my daily life.

Remember that a big battery car is really good at averaging out intermittent usage. If you're plugging into a standard outlet which can only add 40 miles a night, you'll almost always be OK if you average less than 40 miles a day. The occasional 100+ mile day is fine as long as you average less than 40. Only if you need several consecutive 100+ mile days will you need to resort to a DC level 3 charger.