I wouldn't want to be stuck on the homestretch either! But I really don't see that as an issue for either an ICE or an EV vehicle if you are paying attention - especially with one short stop prior. But neither an ICE nor an EV will fix human behavior when someone stops paying attention.I used to drive Philly to Virginia Beach often. The trouble on the trip southbound is that the last 21 miles is on the bridge tunnel. I bought my Wrangler while I still lived in Philly and I never attempted to get all the way home to the beach without stopping at that last gas station before the bridge. Gas light would come on just before and I would fill up.
Mentally I knew I could make it. I'd only put 15 gallons in to a 19 gallon tank and I was getting around 15 mpg, but I refused to be the guy stuck on the bridge needing a tow.
According to ABRP, if you were in my R1T with less range on AT's you would still arrive with about a 12% buffer at Virginia Beach if you made one short pitstop at the Tesla station before the bridge (or threw a few gallons into your ICE vehicle at a gas station if you were running low on fuel).
I'm guessing that the stretch of 21 miles would take about 5 or 6 % from your SOC on the HWY in an R2... The key for me is planning and mapping out a good route (which I would do anyway), but also leaving for your trip with a full SOC, just the way you would likely grab a full tank of gas before heading out on a road trip too.