... I'll literally drive from full tank to around a quarter if I can. That really doesn't work with the whole family, they don't have the longevity in it that I do. I will say your charging times are off at least for Tesla, but I even would get annoyed at the 15-20 minute stops it actually takes, which would likely happen at about the 2.5 hour mark as you mentioned. Basically I see these stops as being fine with the whole family because they'd be happy to get out for 15-20 minutes, but personally I'd rather push the 300-350 mile mark, stop, fill up, hit a bathroom, grab a drink and roll. Now if I could do this, charge in 15-20 minutes and actually get that 300 miles on electric, I wouldn't mind it.
As far as moving from the charger or not, that really depends on where you charge and their rules, which isn't always the same. If you're in a hotel with a level 2 charger, if you get it low it'll take 8 or so hours to charge so it probably won't be a problem of idling on the charger, but you also have to find a hotel with a charger and some parts of the country are more friendly to that and more likely to have them than others.
As far as service issues, that definitely is a case by case basis. If it's not just a sensor, you're likely not fixing it on the side of the road, even with roadside service and that's only in the case that you have a Tesla. I don't know that any other car company offers that, but I could be wrong on that detail.