Luke, I'm going to have to agree with Terry's assessment of what terminology you're using to describe these things. You're not looking for a daily driver. You're looking for a Vespa that you can chain to a lamp post.
I read the post about taking the train into NYC and wanting to have a reliable car waiting for you that still maintains the cool factor (after you've left it sitting for the entire day over and over in a parking lot) and agreed that that would be cool -- but you'd be killing your car.
The sun will eat the dash and roof stitching. The birds will splatter it with guano. Your paint will fade pretty quickly and your chassis will doubtless degrade with that chemical mix New York uses on the roads around you.
I'd say a beater with a rough-and-tumble appearance would be less likely to be messed with, more likely to weather the weather (without its value being flatlined) and should still prove otherwise worthwhile if used in that parked-daily manner. For the cost of a motorcycle, you could get in on this and see if it's really what you want.
Go ugly early, as they say. I don't have a pretty car, and I can leave it literally anywhere with the key on the dash without fear someone will take it. It's so odd to most people that they stand back, marvel at the shape and chat with the next person who comes along about how cool it is to see one.
They're useless to a thief. Their parts are antiquated (yet plentiful), and the cops would spot the car on a flatbed in a bad neighborhood as quickly as they did Whitney Houston's crack pipe in her sock drawer.
IMHO, don't buy a new one. Buy a decent used one for under $10K, since you're a fiberglass guy anyway, and get to know it over a winter. The seats will be cold, the car will mostly behave and you'll either take up smoking while you wait for it to warm up or you'll wear a circle out around it as it sits in that gravel parking lot.
You've been posting a whole lot about the ideal circumstance. Your musings remind me of me, or of Lane, or Max ... You're barking up the right tree, but maybe overthinking the car.
They're not dream machines for the use you intend. They're plastic-bodied, for-pretend go-karts which have huge potential for fun. You're going to get wet. You're going to tear the vinyl. Your car will certainly act up from time to time and -- most importantly for what you're after, you won't have to worry about someone stealing it while you're on the construction job.
Consider any of the used ones on the market here before you go buy a new one. You'll be glad you did, especially for what you're going to do with it.