I live in Toronto Canada where the fun car driving season really only runs from early May till November.
Because of the growing population, stupid drivers and generally inconsiderate people

have increasingly made urban "fun driving" more of a challenge.
I'm planning for my next "fun car" once I've got my garage back. Its currently full up with a boat building project.
I have my eye on two options of manual transmission cars:
- Late 2000s/early 2010s Aston Martin Vantage V8
- Mk 7.5 VW Golf R (half to a third of the cost of the Aston)
I've had "semi-exotic cars" before and been reluctant to use as a regular summer run-about (80s 911, Caterham, TVR Chimaera, etc.). This draws me towards the Golf R. I can leave it parked in the driveway and jump in it and rip to the grocery store or leave it parked anywhere without a worry.
However the opportunity to own and drive an Aston (my Dad owned a DB4 in England in the late 60s) is extremely enticing.
More and more I don't see classic cars on the road. Are others facing the same dilemma in the urban North East with the death of summer classic? I wish I lived in NorCal!