Yes, I'm in Florida. But I was reflecting on my same behavior as when in Georgia. Hmmmm... "finest paint"...? The trouble with assessing such a thing personally is that no one can run "clinical" trials with controls in the home setting. And there a lot of variables. Back when I was doing some house renovation and needing a lot of paint, a Consumer Reports study led me to Valspar paint (sold at Lowe'es) as one of the higher performing brands. (I also use gloss which holds up better than other sheens.) Being a creature of habit, I stick with it. That was a few years back and things could have changed so I don't know how it would shake out now. Maybe someone subscribing to Consumer Reports can update...?

Is the frame wicker or rattan? Rattan holds up very well and should do fine on a covered patio. It's the cushion that won't hold up so well. I have a vintage Paul Frankl rattan bar and 3 stools that has been on my covered/screened pool lanai for 10 years and have had no issues with it other than the stool cushions. I just had them recovered this past spring. The last time I did that was in the mid-80's. I also have wicker resin furniture on the same patio (for a decade) that is still in perfect condition. I do have to get new cushions every couple of years but this set gets used hard daily. It may depend on where you live too. I'm in Florida and it is very humid on my patio much of the time so I deal with mildew. And even though the furniture is under the covered part of the lanai (12' x 25') it still gets rained on at times when the wind is blowing. A couple of times a year I take all of the furniture outside and hose it all down and wash it with a mild soapy solution. We get lots of pollen in the spring and fall. I wipe it dry and let it completely dry in the sun. No problems with either the rattan or resin wicker. This is not my rattan bar but this is what it looks like. Rattan is a very strong material.

I don't understand why you would extend patio/porch to the right nor exactly what you mean by "build a porch that overhangs it" ...?? You might include a quick sketch that explains your intent and also say what the objectives of doing this are. Based on the existing roof line, I can envision such a proposal as being major and expensive. Per proposal #1, you mention constructing a retaining wall that ties in to the porch. I think we would need to see the area flanking the house, as now we're only getting a hint of it. Almost without exception, when considering landscape improvements to a home, it is important to consider the space that flanks the building and not just the space directly in front of it. The best way to show this is stand roughly in line with the center of the house (as you do in your second picture), pivot the camera leftward in order to see that portion of the yard, including the leftmost 1/3 of the house. Then, pivot rightward and take a second picture aiming straight at the house. (You already have this picture.) Then, pivot further rightward and take a third picture that shows the right-most 1/3 of the house including the right portion of the yard. These pictures are all taken without relocating, from the SAME viewpoint. Moving to different locations to take them destroys the possibility that they can be "cut" and "pasted" together in order to make a panorama that does a much better job of explaining how features of the property relate to one another. Sometimes people try to condense the effort into a single computer-generated panorama, but this does not work because it radically distorts the images and removes too much of the detail. @Emmarene, I think the door only looks off center because the point of view of the camera is lined up to the right of the door, not with the door itself. Phil, in raising the porch, you'd need to shorten the columns or replace them. Just guessing, but they look like standard 4" x 4" wood posts that are clad with "one by" material. If that's the case, they could be easily cut while you temporarily support the roof overhang.

I don’t think this is going to happen without serious revamp of the roof . Under the gable no problem you could do a gazebo type structure , a motorized awning almost anything but the other died has no space above the windows for any thing . I think on that side umbrellas are gling to be the answer.I would probably enlarge the deck off the gabled side and build an actual gazebo type structure there and use umbrella for the rest.