Craftsman style becomes the solution

When we began contemplating the upgrades we wanted to make, we hit a bit of an obstacle. We both really liked the cedar shingles used for the gable ends, but adding insulation to the exterior to bring it close to R-20 meant ripping all the exterior coverings off. Although the profit we'll make on the sale of this house will be enough to fund the upgrades, we're not made of money, and at $5.00+ per sq ft, that shingle-look siding is out of our price range. So are cedar shingles themselves. We were concerned that removing and re-applying the shingles would damage too many of them.

Remember that housing project with the Craftsman look DS was working on? Well, it gave us the solution. On the ground floor, we will upgrade the insulation from the exterior. On the gable ends, we will do the upgrading on the inside. We will address the wall variation on the outside by doing this:
That little bit of roof detail between the top and ground floors will hide the inch or two difference. We've seen the framing required on the jobsites and it's tedious, but not difficult. The roofing will come from the roof we remove when renovating the woodshed/carport.

There are many variations of porch supports in the Craftsman/Bungalow style. DS and I have decided that this is the look we prefer, more or less:

With that in mind, here is a view of the woodshed/carport as it is now,and more or less how we envision it once the changes are made:

Just add some gable detailing and windows, and you get the picture. I admit, my SketchUp skills are very rudimentary, but I'm working on it.