The Model S isn't the most reliable, but you know you want one so go for it! I placed a $1000 deposit on the Tesla Model 3 and I'm super excited!
"Reliable" and "Jaguar" don't go in the same sentence. A family member had a 2002 Jag XJ8 and she loved it until it kept on stranding her on the side of the road. Everything from overheating to blown water pumps to electrical problems. Finally last year her transmission failed so she sold it broken for $1000. Now she drives a 2017 Toyota Avalon Limited Hybrid and she couldn't be happier. I owned a 2000 Jaguar S-type for 4 years. It was about as unreliable as the XJ. Every month I would have something go wrong; usually it was a window motor or the window would fall into the door. I went through two water pumps and I had a lot of interior electrical problems and glitches. According to numerous websites, history, and personal experiences, Jaguars are notorious for their unreliability. Add to that their crappy dealers (which may vary) and bad service and you don't have a very luxurious car. The technicians always lied about unnecessary repairs. They are great to drive though and they are beautiful.
Cadillac reliability has improved a little, but is still recovering from their reliability pluge from a few years ago, mainly having to do with the CUE infotainment system, which they have updated since. According to Consumer Reports' reliability survey, Cadillac is on their "least reliable" list at #21 out of 29 automakers. Plus, Cadillac's only real competitor to other luxury brands is the CT6, which is a really nice car.
So my recommendations are:
2017 Tesla Model S ? Who doesn't like that car!? Really expensive though:( Might want to wait for the Model 3, which starts at $35,000 and $27,500 after incentives (in California at least).
2017 Audi A4 ? Audi reliability is #4 out of 29 automakers. Pretty impressive for a German car brand. Car reviewers say this car is one of the best driving cars on the road because it drives great and is comfortable at the same time. The exterior styling isn't out there, but it is elegant and understated, much like Jaguars.
2017 Lexus GS ? The styling is a little more out there. Lexus is #1 out of all 29 automakers CR rates for reliability. It's not an old man Lexus either, especially if you get the GS F. The GS F has a 5.0L V8 with 467 HP. The GS has Lexus's standard active safety suite of features and a 12.3 inch screen for the Lexus Enform infotainment system. It costs less than the German competition and has a great balance of handling and Lexus luxury. The interior is plush and AWD is available, but only with a 6-speed auto. An 8 speed is on all the RWD ones. Paddle shifters are standard on all non-hybrid models.