I am interested in knowing more about your experience driving the Y and the difference between the S and Y and how they drive.
My daily drive is an S-class and I am thinking of enjoying a Tesla Model S for the first time though I have really very poor expectations but will give it a try as a car guy. Also, how about Model X?
Glad to provide input. All opinions are just mine. I may gore a few sacred cows.
You touched upon something that I think is very important; expectations. By knowing what you expect, you can quickly ascertain how likely, or not, you'll be disappointed with a given Tesla model.
My first one was a Y long range, aka MS LR. Flat out, I'd never buy a Y again. I could write a book about it but I don't really need an SUV/CUV and what you give up over the 3 in day to day fun, efficiency, engagement, etc. isn't offset by the increased utility of the Y. That is merely my subjective opinion. Tesla once said that the 3 and Y share over 70% of the same parts. Well, something got lost in the translation, I'll tell you that. The dynamics of the Y are clumsy at best. It really was a boring car to drive on a daily basis. I even added acceleration boost which tuned it up a bit but still pretty boring no very long and the efficiency was pretty bad. After about 6 months of ownership, the values were skyrocketing and I sold it at peak oil and bought a M3 LR.
Ordered the refreshed Model S long range, MS LR, at about the same time. So much better than the MY LR I couldn't believe it. While it was bigger and heavier, it did feel more agile. Acceleration was vastly better. Having a hatch I pretty much had the utility of the Y. It wasn't so ugly as the Y that only its mother could love it. The Y always reminded me of a puffer fish in the middle of inflating. The S always looked good to me. I had things I appreciated a lot such as ventilated and cooled seats, air suspension that I could dial in for comfort or handling, and adjustable ride height. My MS LR had better efficiency than my Y and with a bigger pack had a much better range. All in all the S was more upscale but not what I'd call luxurious. The 3/Y obviously shopped at the Ikea school of interior design. My S came with the yoke which I hated, tried it for a while, and still hated it. I finally sold my MS LR because it never delivered on its claimed performance. At the time I ordered, it wasn't worth the 50k upgrade to buy the Plaid.
Once I decided to jettison the Y, I ordered a 3. It arrived almost simultaneously with the MS LR. Unfortunately, there was a delivery issue with the S so by the time it was fixed I'd already driven the M3 LR a lot more. I had almost immediately added acceleration boost to it which had knocked about a half second off its 4.2 claimed 0-60 time. The 3 in this guise was almost everything I had hoped the MY LR would have been and more. Almost every time I get in the 3, I enjoy driving it. It is the closest thing to Miata Tesla currently builds and is an awesome platform to tweak. The efficiency is great as well. The Y driving it the same way as the 3, got about 30-40% worse efficiency. My 3 rode better with stock suspension than the Y, handled better, was quieter, better headlights, and a bit more legroom up front but less in the rear, a lot less if that matters. I ultimately upgraded the suspension to coilovers from MPP and the car is just an amazing daily driver. It would have been my favorite daily driver if I hadn't bought the Model S Plaid.
As I mentioned I was frustrated, that is putting it mildly, that the MS LR didn't meet its claimed performance specs. That grew and grew until I finally started shopping for a Plaid. I was originally leaning toward and X Plaid but once I found out the middle seats didn't fold flat, I tossed that idea and ended up buying a S Plaid. All the basic benefits of the MS LR but without about 50% more power, a carbon fiber trunk spoiler and track mode. Also included at no extra charge is the ability to out-drive your brakes. The track mode is a blast, you can read up on it elsewhere. Hands down it was worth the extra money for the Plaid over the LR if the word performance is even in your vocabulary. What they don't tell you is if you really push it a lot, and do repeated braking from high speeds, you might want to invest in the track pack brakes. I did and worth every extra dollar. The Plaid's performance is just phenomenal for a street car that has a full warranty. See the vid at the end of a line up against a Chiron from a dig and a roll.
Let's talk about the X. I'll easily take the S over the X if I don't need the extra room. I've had an X for a loaner several times and put a fair number of miles on it. I personally feel that how much better the 3 is to the Y for daily driving, the S to the X is the same way. The X is crashes into bumps that my S mostly ignores. I had them both in the same ride modes. I think the falcon wing doors are a gimmick and just something else to break. I do like how you can remotely open all the doors on the car. That isn't enough for me to buy an X though. If I had to tow something though, and I wanted a warranty to do it, then I'd have to consider and X or Y. I said the heck with that and just put a hitch on my 3 and it tows well. If it breaks from towing, it will be my responsibility but I doubt that will happen. I had no issues with my Y and the 3 is similar enough I am not worried.
So it really comes down to expectations and what you want the car to do. How do you plan to use it? Do you want massaging seat and telescoping thigh support? Do you expect service to coddle your butt everytime you come in? With my last AMG Benz I was always treated well at the dealership. Not going to be the same experience with Tesla. Find someone good at your local service center and hold on to that person and deal with them every time.
So buy a Tesla if you want a car that is pushing the state of the art in a lot of areas. Be prepared to be a beta tester of sorts. Keep in mind the ecosystem is constantly evolving. Expect them to get 90-95% of the basics right. Sometimes that last 5-10% can be infuriating. Expect Tesla to change something at any time, could be better, could be worse. Be prepared for a car unlike almost anything else on the road with so many others trying to copy or surpass it.
I don't drink the Tesla Kool-aid. I borderline hated my Y. My wife says I shouldn't use hate so I'll say I strong disliked it. It could have been so much more. Sure the market sucked it up but many of the buyers are just lemmings. I'd rather tow a trailer behind my 3 for when I needed more cargo space than make all the sacrifices I did to have the Y. The Plaid is just on another level. It is the performance bargain of the century. Did they get it all right? No, but I was able to address my concerns about the brakes. Do I need any more luxury than it provides? No, but I am at about the minimum level of luxury I'd want. The 3 and Y are seriously lacking in creature comforts. With either S and my 3, I can pretty much get 300 miles out of them on a full charge. That assumes I'm not driving 80+ mph. The MS LR, I could do 80 mph but it had smaller wheels than my Plaid (19" vs 21") and that helps the range a lot on Teslas.
As for the S vs Y, the S is so much quicker, handles nicer (more planted and higher levels of grip), generally feels more composed, is more comfortable, quieter, feels a lot more upscale, and looks 1000x better to me.
So of all the current Teslas I've driven I'd rank them as follows for the fun to drive. Just my list and others may disagree.
MS Plaid
M3P
MX Plaid
M3 LR w/boost
MS LR
M3 LR
MX LR
MYP
M3 Std (RWD)
MY LR
Glad to answer any questions and feel free to DM.