Use story poles that you can move (tall bamboo poles set in coffee cans of concrete will work) and some string to outline your addition. Hire an architect to get ideas about form, function and appearance. CHeck with city hall about setbacks, permits, neighbor permissions, and other local code requirements before spending lots of time and money.

You want to walk through the lanai as your main entrance?

No, but there really isn't much choice. If we confine the screen to one side of the front door or the other, it will be too small.

I always think of a lanai covering a pool. How about one covering the patio at the end of the house? Then do a pergola on the front side. Paint the first and second stories to match for less contrast. Can you match wider frames around the first floor openings?

We can't affordably screen the deck between the house and guest house because they aren't squared up to each other, they are two different widths, and two different elevations. Also, the facing side of the guest house is flat and the side of the house is a peak/gabled end. The screen guy said it would have to be completely custom and cost around $11k. The plan is to remove the siding and have the whole house stucco'd, then painted the same. The two sets of sliders will become french doors. We were thinking pergola for the deck so we don't lose the view of the trees when floating in the swim spa that will be half sunken into the middle of the deck.