Well, it's definitely a better bet with the manual from that era--those early F1 transmissions were problematic. I just don't know if I would buy any older Ferrari unless I was a good mechanic myself--maintenance costs alone (not even thinking about repairs) are going to cost a fortune. I've never driven a 360, but my guess is it would be about as fast as a Honda Civic from today (albeit much more beautiful).
Last year I had to briefly drive a 308 (think Magnum, PI, for those who aren't up on Ferrari nomenclature). It was nerve wracking, since it wasn't mine, but also...not fun. Manual transmission was very finicky, no power steering did not make parking much fun, and not particularly fast, either. And this particular one seemed to be in excellent condition, so it's not like it was a beater.
The modern ones may not be classic, but they are thoroughly modern--excellent transmissions, good electronics (gasp!), and quite reliable. New ones come with seven years of maintenance included, and full extended warranties are available for the first four years of the car's life, and after that, you can get extended engine and transmission warranties for another ten years or more. That says something about Ferrari's confidence in their current cars.