I thought about this the other night while having the same conversation with friends. If I came into a large sum of money, I would need a system simply to keep me from going crazy and spending everything on cars. So I would have one in every category I feel I needed. I don't think I'd even keep 10, but it'd be rotating stock. If I want another X, I need to sell get rid of the current one.
1. My Integra- Stock. I would drive it occasionally to keep myself level headed and remember where I was.
2. A Daily- 2 door, fun car, but gets decent mileage and I wouldn't cry if I wrecked. Probably something like A5/S5.
3. Winter/Snowboarding- 4 door, 4wd, SUV. Preferable a Willys Wagon with modern drivetrain underneath. Mild off-road capability that would still be decent enough on long road trips. Needed to have plenty of room for all the crap we bring.
4. Classic Convertible- 50s-60s summer cruise vehicle. Maybe a Lincoln Continental.
5.Work truck- Probably a classic rat rod/shop truck style rig I could use to haul crap around, or just tool around in causing trouble.
6. Italian- Anything that could fall into this category. Most likely Ferrari.
7. My next project vehicle- Something chopped and channeled. 2 door Chevy Deluxe, maybe a Desoto. Something a greaser would drive with stupid HP.
8. Factory Five- I love every kit they make, I'd probably owe one of each if I could.
9. Offroad Jeep- Street legal so I could drive it to and from the woods, but amazingly capable off-road.
10. Empty space for my ever changing taste.
Guess 10 wasn't that hard... I'll probably even be editing this list.