Above is my house as it is now…..

I have a 2 story colonial? house that we did major interior renovations and large exterior screen porch addition that we did recently. And we put a new roof on the whole house, including the back porch (not shown here) tied into the new roof on the existing carport (about 42K). I wanted to raise the roof, so we could finish the attic but my husband did not. That was a mistake. Now that we have put the new roof on, it would be crazy to redo it again, in order to raise the roof now (so sometimes I secretly hope that one of the big oak trees in the backyard will fall (without injury to anyone), so I can redo the roof again.

Anyway, so instead Im thinking of extending the portico out farther, and then building on top of it. I'd like to build a new roof on this second story addition/portico extension with a cross gable that is higher than the existing gable roof, so that I can make this part 7.5 ' or more in order to finish some portion of the attic and add two dormers to the existing roof as well. I know where I would put the stairs on to the attic. I have a big chunk of space I could take from my son's giant walk-in closet that he doesn't need.

Id also like to extend the concrete at the current front porch left and to the right, and covering it with an posts an arbor on each side (rather than a full roof bc I don't want to block the light), and to change the front windows to french doors.

Inside the house, the second floor is four bedrooms with the stairs and hallway in the middle of the four rooms. So, that window on the second floor in the middle would come out, and I'd like to make it a double window and then put smaller clerestory windows on the two sides of this new second floor addition. And, I'd still like to have a portico below, so the entry way would also get a little bigger, and I was thinking of having double doors, or at least a really large door.

Below is a picture of kind of what I want to do, not in terms of style, but in terms of having a porch/portico/2nd floor/attic expansion. My idea, for the second floor would be different in that the new second floor portico extension would not be so wide, so the top part of the peak would be similar to this pic, but then instead of the roof line continuing down to the far posts of the porch, it would be walls going straight down.

Thoughts? Better Ideas?

Im thinking this will cost between 150k-300k. Am I way off?

Is there any reason why I should not do the higher cross gable? Problems with that? Better ideas? Also, have read something about using a crane to lift off your roof, and build walls higher, then put the roof back on. Anyone done this?