My impression is that 500s are overall pretty reliable, but prone to minor niggles. If you have a tolerance for that (which I don't), probably not a bad choice. They are tiny in the back, but it sounds like that doesn't matter.
I have had a Seat Mii, which is the same as an Up. They make an annoying slapping noise when you change gear but, other than that, are good little cars. Incredibly slow and hopeless on the motorway but good fun around town.
Our current small car is a Renault Twingo. The Renault name tends to cause the same feelings as Fiat, but we've had no issues with it at all. It's very good round town, has an absurdly small turning circle and is (in the 900cc version we have) much quicker and more capable on long journeys than the Mii.
If you want tiny, I'd suggest looking for a Toyota IQ. Think a Smart car but Toyota reliability.
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