This dog must be very well loved by his family; not many doghouses have ventilated attics . Notice the continuous ridge vent. There isn't a soffit vent, so I wouldn't consider this venting effective.
I often wonder when I see these giant rat traps, if it is a sign of the home's condition. Sadly, it mostly is.
Flashing is something that I see missing in one place or another on most homes. The most frequent are on attached decks and roof/sidewall intersections; especially at a wall that continues as the roof terminates, there should be a kickout flashing to push water into a gutter or at least away from the siding. I have never seen a proper kickout flashing installed in northern Michigan.
A kickout flashing should look like this. It will be one of the first flashing details the roofer or siding contractor (should) installs. Water travels where gravity tells it to, so the kickout flashing is overriding gravity to get the water into the gutter. Otherwise it would wind up behind the siding(bad).
Notice anything about this picture?
Ok, I'll give you a hint- This is an inside corner. You shouldn't be able to see the structure.