I can understand his situation completely and would probably never consider a newer Ferrari because of the depreciation concerns that he points out. I imagine that the situation is different for anything older than, say, a 328. At that point the cars are all so old that rigorous documentation of services is rarely to be found (and the cars themselves are simple enough that mortals can work on them).
While Ferraris and DeLoreans are both attention-grabbers, the type of attention one gets may be different. I think some people may be predisposed to dislike the owner of a modern Ferrari because of the image of conspicuous wealth that it projects (justified or not). In my experience that isn't true of the DeLorean because I think everyone is aware that they're not particularly expensive to buy. I've found the reaction of the general public to the D to be overwhelmingly positive, like one would get with any other quirky car such as a VW bus or a Citroen 2CV.
As far as attracting women goes, I think guys who buy a car (or any material object, for that matter) for that reason is misguided. It just doesn't work and probably never has, at least not in the way that they hope. That being said, the D is not so much a chick-magnet as a people-magnet and approximately half of people are women.
Now I DO use my D as a real car. I live in the country and often use it, especially on weekends, for everyday errands. I don't often drive it into the city for work because the heavy steering, marginal visibility, and great width make it a little tedious. It's not unusual for me to put on 150+ miles during a nice weekend. I suspect that I would probably use an exotic, if I had one, in much the same way.