You're right, the S is MUCH better looking than the Y. The interior feels much nicer too. The 3 and Y just feel very very overly simplified. I know that's the whole minimalist look they're going for, but I'm not a fan of that for $60k.
Get a Facelifted P90D . Ludicrous is nice, but don't let it be a deal breaker if it doesn't have it. It's still insanely fast without ludicrous.
I'd say P90D, Premium interior, Premium sound. That should be your minimum. I'd also strongly recommend the air suspension, but if you're cheap, the old coil over shock suspension will require less maintenance, probably.
Buy used directly from Tesla, because they reset the warranty back to 4years/50k miles.
AP1 is great. I have it, and use it every day. It works well on the freeway, and I've made road trips of several hundred miles without ever turning it off. It's also fully mature, so you don't have to worry about firmware updates messing it up. It won't ever stop for stop signs or take exits, but it will change lanes when you click the indicator (a FSD feature on new cars), and to be honest I enjoy driving and it's not a "burden" actually having to make my car go using my own human foot.
You can always upgrade the MCU if you feel like watching netflix in your car is important to you - it's not to me, so I'll just have the memory changed for a couple hundred bucks down the road.
With all of that said, my priority was speed when I bought mine. I charge at home every night, so range wasn't really a worry - and I'm happy to sacrifice a few miles to go faster. Your priorities may be different, but those were mine, and it led me to my P90D.