I definitely don't like the attachment method at the windows on door #2. I like the pergola and would recommend making it free standing with bracing and post bases. Normally a pad would not take the weight of a deck or a room, but I think you can get by with a light structure like this.

Having only two legs in the middle may have a tip factor in the wind and may not be the best design. Attaching it to a house only invites leaks in the house if not done properly.

 

Attaching the post ( ledger board ) to the house is why i trying to stay away from option #2. i will the two post because it will have nothing to do with the house and i can dig a 24 inches hole and use concrete for the 2 post.

I'm central FL, so high wind is always a factor. =(

 

Why can't you go 4 posts?

 

We built a couple of swings for a retirement community. All he had was a picture he took in Savannah, so I had to basically design it from scratch. These posts all go 3' below grade, so it is quite substantial. You don't want grandma launched off the front of a falling swing You could modify the top a little wider with a solid roof.