Right now our road trip process would not fit with what is suggested with EVs. My wife like to get the drive over with and many times I'm fighting a bit to stop even at 250 miles. In essence unless we need to have a bathroom break she'd rather just go. So that usually means 4-6 hour stretches between stops. We also then will work to get fuel/bathroom/food stops done at the same time to minimize stops. It's possible for an EV (which she if very pro for. She drives a Prius now, 2011 which we bought used in 2017) she might change that stance but every 150 miles? It seems a big move for her, but she might surprise me. For this last trip for example, we left about 6 AM, did not stop until about 11:30 to eat lunch and fuel. It was fast food so perhaps 15-20 minutes. Then we stopped at about 3:30 next for bathroom and snacks, so perhaps 15 minutes. Then made it to our destination at 6:30 (there was time change in there so was really 7:30). That would not have worked with an EV. She was OK with that trip. When we head down to Disney (which will happen less now that kids are grown) we leave at 2-3 AM and arrive late the same day so between 16-20 hours of travel depending on stops.
If you (or your wife) is absolutely set on having this kind of long-haul, 600+ mile road trip with no wiggle room to fast-charge along the way, then no, current EVs won't meet that need. But since you seem to want to stop a bit more frequently, having an EV might force that issue.
To give you one example of what that might look like, a VW ID.4 will give you 250+ miles of range in non-freezing weather (rated for 275, so some cushion there for highway speeds). It can give you an additional 200+ miles of range with a 150kw DC fast charger in 38 minutes. Planning on two stops of ~45 minutes each you could easily cover 600 miles. That would be 3.5 hours of driving, break, 2 hours of driving, break, and then arrive at your destination a couple hours later. Total travel time of 9 hours. It wouldn't meet your 16+ hour marathon trip to Disney, but such a trip could be done (maybe) if you are willing to take 4 breaks (breakfast/lunch/dinner and one more?). TBH if that were me I'd want an ICE vehicle (rental?) - but that also sounds like a terrible idea to me regardless, and my back would be screwed up for days afterward.
A better question here might be how frequently do you need to take these marathon drives, and will you allow that to determine your vehicle selection.
The daily commute needs at least 60 miles round trip and if there are more stops (different students each day of the week) could be more but probably never more than 100. So it seems that the 120V would not be an option. Not sure what all the costs would be to get the 240V service added etc. I can work with electricity in the house, wiring up ceiling fans, changing switches, outlets, etc. but for something like this I do not have the knowledge to even know what I don't know. I know our current service is 100A not 200A that you see in some homes, so I assume I'd at minimum need electric company to expand that and would need to research those costs with them.
Installation depends on what you buy, and most people are coerced into buying much more than they need or want for home charging. Consider whether you really need (or want) a 'smart' EV charger with a snazzy interface and phone app, or if you just want to plug your car in and have it charge. hint: every EV I know about has built-in charge management so you can schedule charging during non-peak hours anyhow, (making this 'feature' of most smart chargers entirely redundant). 'Smart' EV chargers also require a solid WiFI signal and many (most?) will sell your data as part of the package, which you may or may not be ok with.
You can buy a L2, 240v charger for around $350 off Amazon. If you are even remotely handy you use a 12awg (or 10awg) extension cord and swap out the plug. For the installation, all you need is the circuit and receptacle. The installation is however much a certified electrician will charge you for installing a 30, 40 or 50amp circuit, which depends greatly on your location, your existing panel and service, and how far and how complicated a run it is. If it's a short run from your panel to your garage (or outside) I'd expect to pay between $300-500 for the installation, including the breaker. If your code requires AFGI breakers those can cost $120, a short run of wire is under $100, and the equipment is $350 or so. The rest is just a few hours labor.
100 amp is more than sufficient to add a charger to most homes. You might not want to put in a 50amp charger, but that's overkill for almost everyone and certainly for your commuting habits. A 30amp (7.2kw) home charger will add 15-20 miles per hour of charging. Plug it in for just 6 hours and you're going to replenish even your 100 mile days with ease.
This is not an imminent thing for us. I'm hoping to make it to at least 2025 with my existing car to over 200K miles perhaps, but will likely stick with it until it dies and the cost to repair exceeds the cost to continue. I figured that would allow the newer models to be introduced, be tested in real world conditions and it can help me make a better decision, but it seems that it is not going to be a cost savings no matter what so I'd have to justify the move based on lifestyle, climate impact, etc. from what everyone says.
Well you probably just want to check back and see in a couple of years if you aren't going to buy one now. Two things which seem to keep improving are DC charge times and the (often expensive) options for ever larger battery packs. Also, the number of DC fast chargers is growing exponentially right now. A few years ago the most juice typical EVs could take was 50kw. now a number will go 125kW (and Teslas at 150kW). There are some cars that claim they will be able to charge at 350kW in the coming years, which in theory could add 300+ miles to an extra-large battery pack in the 20 minute range, IF they can figure out how not to blow the entire pack up during the process. Likewise, there are a few groups claiming they can reconfigure existing chargers to go from 20% to 80% (roughly 150 miles) in about 10 minutes.
For now the existing range and charging infrastructure is more than sufficient for >95% of drivers. but you sound like an extreme outlier - someone who does 16 hour road trips and won't compromise on breaks or distance. It is what it is.