Are classic automatics a minefield?

I am interested in purchasing a 20th century classic. I can drive manual cars but much prefer automatics and was wondering if there were any classics, built with automatic ‘boxes that are reliable and...

I'm looking for a classic car to run around the city - what's a good buy?

I'm looking for a classic car to run around the city - reliable, easy to park, won't rust away at the roadside and able to stand up to lots of stopping and starting. Probably automatic. What do you suggest?