[sd_boxster]

What kind of weather will you be driving in? If you expect to have to use it often in the rain, I'd go with the Cayman. How safe is the neighborhood? It's easy to slit the Boxster canvas top and steal things.

If I lived anywhere other than San Diego, I would have probably gone with a Cayman. However, the weather here is as ideal as can be for a convertible, it's always garaged, and I never have to drive it in the rain.

The cars are arguably equivalent in all regards except whether or not the top comes down - so you need to determine whether the convertible top is an asset or a liability and decide accordingly.

At the risk of making a gross chauvinistic generalization, women love convertibles. So the sisters who will be contributing toward the payments will be happy, and the brother(s) might also find the allure of a fine German convertible to be an asset.