car and house
Houses usually appreciate, new cars usually don't.
I think you may be applying traditional wisdom to a non-traditional situation. At least in this part of the country, 99 times out of 100, a "typical" (cookie cutter in planned community) brand-new house will see an immediate depreciation hit, much like a new car. Except in this case, the depreciation hits as soon as the house is mostly completed, not when someone first buys it. I don't know this, but I suspect the two main reasons for this depreciation are 1) the advantage of getting exactly what you want is lost and 2) the new home builder pads the build-to-order price to cover contingencies. Any way, a cookie-cutter house that a local volume builder here will build you today for $250K would immediately resell for perhaps $225-$235K.
This depreciation is further an issue when you get into full custom builds in less cookie-cutter/planned communities. The builder probably loses any economies of scale, and they can't reuse plans like a copy machine. And, buyers' expectations to get exactly what THEY want goes up.
As a more specific example, one area we're looking at is mostly built out, but has one lot that someone bought to build on later, but ended up not being able to. The average resell price in the area (lot + house) is approximately $150/square foot. I estimate our cost just to build the house will be around that mark. So out of the gate, we're down anywhere from $60-$120K (i.e. cost of lot). There may be a modest premium to be gained by having a newer roof/HVAC/etc than all the surrounding homes, but there is also the somewhat deviant style and significantly smaller size cutting the other way.
As far as appreciation goes, RunningBum has hit the nail on the head. As we all know, history is no predicter of the future, but cookie-cutter homes built in our neck of the woods 10-15 years ago are selling for about what the original buyer paid to have them built. And they typically are going to have had money put into them in the meantime -- new kitchens, finished basement, landscaping, etc. Higher-end semi-custom and full custom are selling below what was originally paid.
PErsonally, I don't consider a primary residence as an investment. So I think my car-house analogy holds water. Most of us need a house and most of us need a car. In my hypo, we are considering spending more than necessary to move from a need to a want. Purchasers of both items pay a premium for brand-new in the form of an immediate depreciation hit. Purchasers also take a hit for going more custom, too. Depreciation is pretty much guaranteed for the car and has been the case for houses here, too. Admittedly, during other periods, modest (e.g., 3% annual) appreciation of houses is possible.