The emblem in #8 looks a lot better but I'm having a hard time seeing it on a sign at the entrance to the community. The sign will probably be either stamped into metal or etched into wood. Can you create a simplified (maybe colorless) version of the emblem?
Also the font is still a little too Irish feeling. Gig Harbor is more of an upscale community in Washington State and I just don't think that font will work. Take a look at the city of Gig Harbor's website if you want a better feel for the area. http://www.gigharborguide.com/
I understand your concerns. My day job is the owner of a Sign Business. You have a lot of possibilities with this logo.
A) Sandblasted Redwood B) Cast Stone C) Combo of Sandbalsted Logo icon and Archetectural cut letters out of aluminum, trovicel, acrylic, etc.
Type styles need to be bold so your signmaker can maintain strength of the letters and other elements. All lines of the logo need to be simplistic for the same reason. Colors can be modified according to the inteded use. For print material in real estate listing you could go with the full color or the simple black and white. L
Let me know if I am on the right track now. I will have plenty of time over the weekend to submit other ideas. Thanks for the Feedback.