I've always been desirous of a little British roadster, a'la an MGB or Triumph Spitfire, but lacking any mechanical inclination whatsoever and not having deep enough pockets to have a mechanic on personal retainer, I have wisely resisted. Recently, a family member who buys and sells cars gave me an opportunity to pick up a high mileage, but well running Miata. These cars definitely have the look and feel of a classic roadster and are tons of fun to drive. At the price I picked it up, I figure I can get my money's worth no matter what happens.
A good friend who has been driving classic sports cars for years had this suggestion. Upgrade your AAA membership to plus(100 mile towing radius), don't take it out if you absolutely must be somewhere on time, and if you end up on the side of the road waiting for a tow, keep a good attitude about it. With that in mind, I took the plunge and have been having a blast ever since.
If you are a would be Miata owner, be sure to look in on Miata.net. Great resource.
My 1995 Black and Tan