It’s a tough question. I now feel comfortable with my 19 years old, 13k$ BMW but it wasn’t the case 7 years ago. I came to realize wrecking it wouldn’t crush me financially so I came to be comfortable using it.

However, at one point I considered buying a cheap-ish Vantage (35k$), which was a bit of a reach for my budget. Then I factored in insurance, gas and maintenance. At that point I realized it’d cripple my budget and I’d be afraid to take it out, which defeats the point of a cool car.

So I ended up with my 280Z that was initially way cheaper but will end up costing more than the Aston after the restoration, but since I can DIY maintenance and insurance is cheap I’ll run it with some amount of peace of mind (until the first ding on the new paint).

I think how prestigious the brand is also counts. Jealous stares in an Aston aren’t as good as thumbs up for a classic everyman sportscar you put sweat equity into.

I think I’d draw the line before a 911. A Cayman would be my upper limit I think. Used off course.