Hey There: the best way to update your rooms is with battery operating remote controlled roller shades. The roller shades go up to 160 inches in width, the batteries have a life time of about 5000 to 7000 circles and are shelf DD batteries - so there is no expensive replacement. The installation is easy as a manual roller shade...no costly hard wiring and installation is needed...all shades are pre-programmed from the German manufacturer...

Consider building building your patio the width of and in front of the roof line on the LEFT with a "greenhouse/sunroom" (clear or semiclear) roof that is above your upstairs windows but beneath your roofline. You could have a gentle slope to the roof to move rainwater away from the house but your patio roof would not need to be square or rectangle; instead, you could create the shape of five sides of an octagon. You could have a ridge in the center of the patio roof closest to the house -- a ridge parallel to the two sides of the patio roof that are at a right angle to the house -- sloping the patio roof to left and right of that ridge. Then you could use the end of the ridge farther from the house as a center point from which you could slope the roof in three directions forming the three other sides of the octagon shaped patio roof.

Impossible to say from Market to Market. If you stay within the confines of the current window footprint, you should be able to do this from a standard window/door contractor vs. a GC. What is on the outside of the window in term of siding, brick, etc.?

He'll need an 84" length, or, if unavailable, a 90" length of drapery, which may require hemming, to "skim" the floor. A one way draw would not work, as he lacks sufficient wall space on either side of the windows to stack the drapes. However, he ,may be able to locate a custom rod which would cover windows on both walls, yet open to the right. The least expensive option may be through Ikea, who offers some better window coverings for significantly less money. Given his fabulous view, he may want something lighter weight, admitting light, while still giving some privacy at night.