Noobie

I have a 2023 LR. Not much to say. Just make sure the tires have good tread and there is no obvious damage.

Try to get a 2024 so you can get HW4.

It's a great car. Even after 6 years and more than 140000 km my Tesla puts a big grin on my face every day. I would look for a non smokers car with a low consumption. As this is an indication of how smooth and soft a car was driven. I am at 160 Wh/km. And that's even with german Autobahn

I would put more money to 24 because of HW4, ambient lights, heat/cool seats.

Isn’t 24 the highland?  There will likely be a pretty big price difference between the two (given same miles and everything else).  So you’ll just want to choose the model you like better (highland got a lot of great upgrades and almost zero downgrades except maybe the front depending on how you feel about the look), and what you’re willing to pay, of course.

I loveeee my 2023. I'd recommend the 2024 so you're on HW4, but I have absolutely zero complaints. I have white interior and have never had a heat problem without the air-conditioned Highland update. I'd have an issue with sand getting into the vent holes (the dog loves the beach!), and I don't care too much about having a screen for the back seat. Test drive both. You'll get used to turn signals without stalks after some use. I think you'll be happy with either but you'll be more excited about HW4 if FSD is something you really enjoy. It's just fine on HW3, but it meets my needs.

Make to sure to budget money for the insane insurance these cars punish you with. These cars might be super cheap to buy used, but you'll end up paying more in insurance than the car is worth.  Just ran the numbers with two of my insurance companies, both more than doubled my current premium for a model 3. That is absolute insanity. Like just absolutely absurd. I can insure an exotic car like a Lotus for as much as a Tesla model 3. That ain't right.

Interesting because that's one thing that never crossed my mind. Hopefully being 50 will benefit me.

Oh yeah, you should be good. Older people seem to not get hit with insane insurance on Teslas for some reason. My dad is older and I was complaining to him how much it was and he said he pays no more for the tesla than he does his Honda. I would love to lease one for a few years and save some money, cause you can lease an AWD model 3 for less than $20k for 36 months. But with insurance makes no sense

Make sure you actually need the LR, saves some money if you don't actually need the extra battery capacity.

I plan on making trips from KY to visit family in Florida and Illinois, which is the only reason I figured I needed LR. Other than that, I just go back and forth to work, which is around 70 miles a day.

I'm 44 and bought mine a little over 2 years ago, my insurance premium increased less than 24 dollars over 6 months. I think you'll be ok.

I'm going to be contrarian here and say that you should go for the '23 over the Highland '24, simply because it was the first model year of the Highland redesign. For the '23, they had multiple years to work out the issues associated with the first gen. I had a choice similar to yours, and I don't regret choosing the '23 at all. If you are dead set on a Highland, I understand, but go for a lightly used '25 if your budget can allow it.