I've Had Terrible Luck With Cars! What Should I Buy?

Well, Tim, I was all set to recommend an EV for you. You said you're open to EVs, it really isn't hard to find gently used EVs with at least 300 miles of range for less than $35,000, and the one I found wasn't even a Tesla. No, it was this BMW i4 that I still think would be a great choice. It has plenty of range, should be perfectly quiet and comfortable for those four-hour drives to visit family, and offers plenty of power for those times you just want to feel something while driving those boring Midwest roads. Since it's nearby and in budget, it's basically perfect for you. But then I saw it. For a mere $2,000 extra, you could buy this 2004 Bentley Arnage with less than 20,000 miles on the odometer. Is it as new as the BMW? Nope. Will refueling on those long drives cost you way more than the BMW? Absolutely. Are the maintenance and repair costs going to be scary? For sure. On the other hand, you already admitted you rarely drive, since you mostly take the train. So it wouldn't need to be a daily driver. Since you won't be driving it much, the terrible gas mileage won't be an issue. And did I mention it's a Bentley? This thing was built to devour highway miles in ultimate comfort, meaning you'll arrive refreshed and de-stressed, something I always recommend when visiting family. Get the BMW if you want to be boring, but you currently own a Mini, so I know you're not boring. So come on. Live a little. Roll the dice on the Bentley.