Bill, this is way off base from sail trim, but that's sort of different from my experience.
A while back, I had more money than I could bury in the backyard, with minimal dealings with the gals.
Recently, when I was spending my days in a long, black, luxury Mercedes, the same. I think they thought I was pretentious maybe? No idea, the incalculable equation. Now, my appearance is a lot like yours, I've seen your picture, and this is by NO MEANS an insult to YOU, but I ain't no Fabio.
I ride around in my old Dodge Truck, that has 312 thousand miles on it, (I'm a good mechanic), and I swear, I can't half keep them chased away. MUCH to my wife's chagrin. Go figure.
I think, in my opinion, that I don't even want the woman that's attracted to a "Mercedes".
My girl now, is from the Westchester area of N.Y., makes more money in a year than I can in 5, and is very cordial, and sophisticated. And worships the ground I walk on. While I've considered having her psychologically evaluated, I think some women just like an ol' country boy...
There's a woman out there, that likes golf "bums", old trucks, and older boats. Knowing "your place", sometimes is the catchall.