Love this question. I'll have to qualify this by figuring that I'd be buying a bigger house, with a bigger garage. Let's say spots for 5 vehicles:
Classics:
1. Jaguar E-Type Cabriolet. Budget $120 000 for one in nicely restored shape, but rough enough around the edges to allow me to drive it without too much concern. Ideally a series 1.
2. 1967-1968 Shelby Mustang GT350. To my mind and eye, the best expression of the Mustang ever made. Figure another $150 000 to get the condition, year, color etc. I want.
Modern:
1. Volvo XC70. Nicely loaded up. Probably one of the best vehicles for my lifestyle. Enough room for dive gear, kayaks, photography stuff, camping, etc. But with respectable handling dynamics and wagon styling. Budget maybe $60 000.
2. Mazda Miata. I wouldn't want anything more in a sports car. Fun. Light. Efficient. $35 000.
3. Tesla Model S. I'd want to invest in all electric technology. This could be the car - gives good range. Good performance. But I'd probably make the judgment call when I had the money. Could be any number of vehicles that fit the bill. Budgeting $120 000.
I guess that'd be it... guess I'd be looking to spend about $500 000 CND.