What does your architect suggest? This isn’t a project that you can do with a some home designer who is really a $99 software geek.

Sleeps 15, right? Drop the transoms on the third floor like apple pie said. They're not consistent with the rest of the house and will be a real pain to clean. And if you want a better representation of what that house will look like, get a drawing that gives you a view from the ground. Right now, a second floor view doesn't help anyone and you'll suddenly be surprised when you see it from the ground.

Commercial buildings require the services of an architect.

Amy, to be clear, the transom is the small window above the larger windows on the third floor. The deck looks fine, part of it covered and part of it for sitting in the sun.

Green, this isn't a commercial building. On the beach it's typical to see a house like this that sleeps 13-15 so two or three families can go in on the $5k+ a week rent.

Do you have an architect? Adding a third floor to an existing 2-story house would be a major structural change.

Have you actually gotten this past the permit office for the height? And gotten a bid that wasn't 1M to do it?

Yes, ditch the transoms because they're not in any other part of the facade, they look like an afterthought. Typically, they're used on the first floor and not on the second because if only one floor has a high enough ceiling to accommodate them, usually it's the first.

It's also a detail that isn't going to be noticed that much. Your looking at representations that are taken from way up in the air. Get one that looks like it was taken from the ground. That will give you a better idea of what it will look like in real life.

Is this going to be a rental? Placement of fire escapes may affect your window designs.