In what order should I complete these projects?
1. New roof.
If you've got a leaky roof, you've got big problems.
2. New Siding.
Since it sounds like you'll be adjusting the thickness of the walls, it makes sense to complete this job before anything else that will be installed on/in the wall.
3. New Gutters.
Depending on what shape the gutters are in, this might move up or down the list.  If they are in fairly poor shape (leaking, sagging, etc.), they should be addressed sooner rather than later.
4. Replace Windows and Doors.
Assuming this is not simply an aesthetic upgrade, new windows and doors can increase the homes efficiency making it an important upgrade.
The Others
The rest of the items on the list are convenience items, and can be done in any order (assuming the deck is not causing damage to the house).