Consider the Fiat 124 Spider. Although considered by many to be more elegant than the Alfa Romeo Spider of the same era, these cars have not held their value as well.
Step2
Find a Fiat 850 for a cute, midengine convertible.
Step3
Look for a Fiat X1-9 for a car that still seems surprisingly modern.
Tips & Warnings
Look out for rust and abuse. These cars were relatively inexpensive to begin with, and not everyone gave them the maintenance they deserved.
Be sure to find a mechanic who has experience with these cars.