Our new roof was put on yesterday (completed in one day).Here is a photo that shows work while it was going on. We decided to go with a layover (no tearing off the old shingles) to save some money. We had one soft spot repaired, and went with the upgrade type shingle, so it still has the 25 year lifespan... and we saved several hundred much needed dollars.
We are going to do the vinyl siding this fall. The new slider is coming in the next couple of weeks (we want that in before siding goes on). We are replacing a French door that is literally rotting, drafty, and leaking (not to mention we do not like how it opens into the house, whereas a slider stays flush with the wall), and that will improve our energy use through the winter significantly, it was that bad! There are a couple other little things that need to be done before siding (a couple windows, and the front porch). We will be able to redo the back deck next year, ourselves. These major exterior improvements (roof and siding) are the most fun - they don't require US doing the work (and it's worth it!).