Originally Posted by thekctermite
I would do the siding and the windows at the same time for sure. The roof and gutters could be done earlier or later, depending on priority.
I agree with this. If you can't do both at the same time, do the windows first. Generally if your home has storm windows the siders will charge you to remove them, put metal trim over the exterior trim and then reinstall them. Then the window company will charge you to remove the storm windows and redo the metal trim/coil stock.
Look into the 0% loans for energy efficient home improvements (in MA) they should apply to your blown in insulation, windows and maybe the siding.
This is a good site for rebate info http://www.masssave.com/index.php