If you were going to build a fancy new car, would you name it a Jugo or Hugo? Not unless you want consumers to remember the Yugo. And you'd have more sense than to name your new vitamin pill Vigara, since another your business growth might not only be base on excitement for your product. So I'm wondering why someone would build a fancy suburban neighborhood and then name it Trailmark, because it sounds an awful lot like Trailer Park to me (and it's exactly what the fancier neighborhoods in St. Johns County will be calling it).
I do have to admit that I'm happy that we've only taken 150 years to move past naming neighborhoods after plantations. Sure, we still have a bunch of plantation-hoods, but names like Wildwood, Nocatee, and Beachwalk at least forego the odd naming convention. It's also nice to see that after 250 years, we might be moving past the other convention of naming neighborhoods after England, like Kensington.
Still, I think Trailmark sounds a lot like Trailer Park.