1000 miles in 24 hours is 12.5 hours of riding at 80 mph average, 14 hours at 70 mph. (Once you have enough charging power, total trip time is reduced by driving faster, even if less efficient)
1000 miles will probably use around 120 kWh. Terry has about 20 kWh onboard, so he needs to charge 100+ kWh in about 10 hours. At 22.5 kW (3 J1772), that's about 5 hours of charging. Barring everything goes smoothly, there's about 5-7 hours of "slack" to locate charging, slower speed travel to/from highways, traffic, etc.
1500 miles in 24 hours is another Iron Butt challenge. That's about 20 hours of riding even at 80 mph.. it'll need significantly faster charge rates, around 50 kW.
Model S85 for reference has about 200 miles of range at 80 mph (400+ Wh/mile), and can charge about 50% in 20 minutes (starting from low SOC) on 135 kW supercharger. It'll take about 95 minutes to drive and charge 100 miles, so it would barely be possible to drive 1500 miles in 24 hours with Model S in the best conditions.
I've done two 1000 mile trips in < 24 hours in my life, both by car. They were miserable, but perhaps with forced periodic stops they would have been more enjoyable (and safer).