Wow, thanks everyone for the very thoughtful replies! I felt like my original post was too long, but I do have some details to fill in on some of the suggestions:
We have discussed aligning visual styling to our primary residence. Our house has cedar shingle, which we were told would be pretty...
My wife and I have lived in a 1915 craftsman house in Tacoma, WA for 5 years now. We've gotten through some priority house upgrades and deferred maintenance - new kitchen, replacing live knob & tube with romex wiring, new roof, exterior paint, new gas insert fireplace. On our house wish list one...