Another vote for new MY LR over the used MS.
You noted that the ride in the AWD non-LR MY was less comfortable than the MS, and that'll be down to the MS having air suspension. Air suspension is costly to repair and something I'd be aware of given the mileage of the MS you're considering. You'll get the most comfortable ride in a MY if you go for the base 19" Gemini wheels. No difference in suspension between the MY AWD and MY LR. Do you remember if the MY AWD you test drove had the black 20" Induction wheels or the silver 19" Gemini wheels?
You also said you'd be doing a lot of road trips. I've driven a MY LR between Houston and Chicago many times and was never concerned about range. MY LR can also take advantage of the full 250 kW offered at v3 superchargers. The MS you're considering may have a peak supercharging limit below 250 kW (This will depend on the build date of that 2020 MS. Some earlier MS Ravens peaked at 225 kW; later Ravens got thicker cabling that allow for 250 kW peak charging.)
One more thing that may seem relatively insignificant today but will become more noticeable over time: the 2020 MS MCU (center screen) has the Intel Atom processor. The new MY is running with the AMD Ryzen processor. The AMD processor is much more powerful than the Intel one; there's a noticeable improvement in UI responsiveness. That's not to say that the experience today on an Intel MCU is bad--its just becoming clear that the software is approaching the limits of what the processor can do. I expect the difference to become more apparent both in terms of responsiveness (e.g., web browser) and new feature compatibility (e.g., Zoom video calls) as time goes on. Something to keep in mind if you're thinking about keeping your car for a few years.
You noted that the ride in the AWD non-LR MY was less comfortable than the MS, and that'll be down to the MS having air suspension. Air suspension is costly to repair and something I'd be aware of given the mileage of the MS you're considering. You'll get the most comfortable ride in a MY if you go for the base 19" Gemini wheels. No difference in suspension between the MY AWD and MY LR. Do you remember if the MY AWD you test drove had the black 20" Induction wheels or the silver 19" Gemini wheels?
You also said you'd be doing a lot of road trips. I've driven a MY LR between Houston and Chicago many times and was never concerned about range. MY LR can also take advantage of the full 250 kW offered at v3 superchargers. The MS you're considering may have a peak supercharging limit below 250 kW (This will depend on the build date of that 2020 MS. Some earlier MS Ravens peaked at 225 kW; later Ravens got thicker cabling that allow for 250 kW peak charging.)
One more thing that may seem relatively insignificant today but will become more noticeable over time: the 2020 MS MCU (center screen) has the Intel Atom processor. The new MY is running with the AMD Ryzen processor. The AMD processor is much more powerful than the Intel one; there's a noticeable improvement in UI responsiveness. That's not to say that the experience today on an Intel MCU is bad--its just becoming clear that the software is approaching the limits of what the processor can do. I expect the difference to become more apparent both in terms of responsiveness (e.g., web browser) and new feature compatibility (e.g., Zoom video calls) as time goes on. Something to keep in mind if you're thinking about keeping your car for a few years.