Question 3... my old ugly house does not have a covered porch.
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Lots of photos here;
https://www.google.com/search?q=build+an+awning+over+front+door&tbm=isch&tbo=u&source=univ&sa=X&ved=0ahUKEwiz9eSmppDUAhVI04MKHZ_jBTIQsAQIhwE&biw=1016&bih=642
I think you have a great idea here! You can find used pallets in several places for free. My local Lowe's store puts them behind the store for anyone to take for free. You could use the pallet boards to cover the roof of the trellis. I think you will need to screw some boards to the house and then screw the trellis to the boards. Maybe you could attach the boards to the framing on your existing door. Good luck!
I have a similar issue I am working on. Your idea does add curb appeal, the problem is that type of arbor will not be able to stand up to any type of roofing material, but there is always that clear fiberglass roofing (pictured below) you could use and plant some type of vine plant to help hide it. I am not sure you could attach it, but you could weigh it down some at the bottom planters. Maybe watch your local craigslist ads for similar used metal arbor.
For my project I believe we are going to either do one projecting from the house or one built up next to it. You can get theses in kits or build them yourself which is cheaper and quite easy. They can also be found on Craigslist, or eBay.
Then use that clear fiberglass I spoke of. (pictured) Home Depot carries it for around $31 a sheet.
I hope you find something that works.
We have vinyl siding on our house and the manufacturer told me that I should drill a hole larger than the screw going into the wood behind and then fill in with vinyl caulk. This would allow movement of siding between cold and hot weather. You might want to check with the manufacturer of the siding, otherwise you could mess up the warranty.