It's really difficult to say what makes financial sense. If you go by earned income, I've almost certainly been below the average (or median) buyer of most of the cars I've bought, but we all have our vices. There are some really expensive habits/"hobbies" some people have that no one really seems to talk that much about, and are arguably as bad (if not worse) than liking budget-bending cars. Regular overseas travel or fine wining and dining, for example... There's certain stigmas attached to certain ways of spending money, but not others, and it's often silly.

I was prepared for the expense of the GT4, but was still worried about regretting it because I wanted it as a track car, and I thought I might be scared to drive it properly because of the fear of sending $100K into a tire wall... Especially when the car started going for crazy prices after I bought it. But that never happened. Once you're actually on the track, you're not thinking that hard, and you're just having fun. And now, years later, I'm less worried about that money, too. <knock on wood>

/lifestory

tl;dr: No I haven't regretted anything yet.