One ultra expensive car or a fleet of cheaper ones?

I want to chime in with Tim here as well. I have done it both ways. At one point my only car was a Ferrari Daytona Coupe. It was a car that I had always wanted until I owned it. I sold it a number of years ago and bought a lot(10) of cheaper cars.

There are two basic problems with more cars. The first is more expenses and more upkeep. The second is that it is difficult to actually find time to drive them. Since I am first and foremost an end user, this is a drag.

I think in an ideal world that the key is to have a car for every occasion. My list would probably be a Aston of some kind, a 911 of some kind, a roadster of some kind and a Bentley, Rolls Royce or series 1 XJ6. That way I would have a touring car, a 911, a roadster and a 4 door British classic. That would be a manageable set of cars that fit each category.

I will say though if I could get my hands on a nice DB5 that I think I would be satisfied with a single car. I think if a single car is that car that you have always dreamed of owning and it is a good car, then one car can work.

I've never had more than 1 collector car but I can understand why a wealthy person would have 1 cobra instead of dozens of mustangs. You would never have time to drive and enjoy them. And imagine keeping all of them running, insured, and licensed.

cwebb64 wrote: And imagine keeping all of them running, insured, and licensed.

Depending on where you live, that isn't that bad. In PA, cars tagged as Classic or Antique are registered once and that's it - you pay nothing more to PennDOT for as long as you own the car. Classic's still require yearly safety inspections, but Antiques are not. We've had many discussions about how affordable classic insurance is.

I do agree somewhat about keeping them running if you can't afford to pay someone. Right now I have 5 classic cars and 3 daily drivers to keep track of and to say it's been a struggle would be an understatement. And even more so if other projects (like a major house renovation) are clammoring for my time.

Just this week I had to throw in the towel and take the g/f's '73 Volvo 1800ES to a shop to figure out a no-start/poor running issue. After 3 days of spinning my wheels trying to figure it out, I just can't afford the time anymore and needed to move on to other jobs I know I can do.