You do have a lot of lights! LED Christmas lights will begin to cover their initial expense very quickly through your power bill.
A large part of your lights appear to be lawn decorations, which would mean that you can immediately begin switching to all LED lights. I would recommend starting with the decorations, because that will allow you to update as few or as many as you can afford to, while simultaneously adding real bang to your display. The roofline will need to be done all at once, and can probably be done once LEDs have been introduced to the front yard lighting display.
When calculating bulb count, it is helpful to know that LED lights have a brighter color than traditional incandescent lights, requiring less bulbs per string. LED bulbs also last years longer than incandescent and are encased in acrylic plastic, so each year you can add to your existing LED Christmas lights
without much need to replace old or broken bulbs.
A final note is to be cautious with color on the house itself. If you plan to keep your white lights, you should coordinate your purchases to ensure you get all of the white bulbs at the same time, from the same company. There are many different hues to the whites, and they are noticeable when placed side by side. It is also recommended you plan for the future and purchase at least one additional box of bulbs or string of lights when making your investment. I would not worry about shades of whites in the decorations.
I look forward to seeing your 2011 display with some bold LEDs popping out!