[Dolle Dolf]

I am very seriously considering buying an '02 Spyder ... I drive 50 miles a day in the Washington DC traffic... My wife will drive the CC as well and can't drive stick.

Teach her to drive a stick. European lasses can. Then buy a manual stick shift Spyder.

The other option I'm considering is a red '98 Ferrari 355F1 for $85k,

Well if you get the maser with the leftover change you can buy a nice Lexus for wifey dear.

but I'm concerned about the daily driving and much higher maintenance costs.

As you should be. Traffic jams, clumsy wives and CC don't work

Also I don't believe the older Astin Martins (which I'm also considering) come in automatics.

I think they do. If you need to share with wifey "old" does not work so well as cars are concerned. I know, I have one too. A wifey that is, not an AM. Why don't you consider a recent Jag XK8, the outgoing model is still a neat car, that can be had on the cheap and still attracts oohs and aahs. You can buy her one as a token of undying affection, and then sneak in your black Maser through the back door for less than the F355.
The new XK looks neat, has a great interior, drives like a bat out of hell, and is half the price of an Aston. You can flap the paddles and wifey can let the auto tranny do the job.
Some people like the Bangled Beemer too :-(