FWIW, I think moving the 3rd floor stairs to the chimmey side preserves your wifes' window view, avoids the head bump, and saves deck space if the rise/run of the stairs can be made to work.
If you want to preserve fire egress via the third floor, I doubt you have much practical choice other than to run the 3rd floor deck out to where it will be supported by the brick columns or a beam spanning those two columns. If you don't really intend to use the 3rd floor as a deck, there really isn't much point in making it any larger than it has to be to span that distance. Visually, you would want it as symmetical as you can get it relative to the two windows and the door. In other words, don't chop it off in a way that makes it look lopsided.
Before building anything, I'd draw it out on the most recent photo you made showing the house with all of the decks removed.
View attachment 831475
Your line of thinking makes complete sense, and we looked at doing it that way with the contractor when he first came out to look at the job. The issue is per your rendering in the picture, the wood portion of the stairs under the "added" deck in purple you added would need to be extended further left (no way with the room and the first set of stairs to tie in additional steps from the 3rd floor with the space there to work with). See below, orange line below, this is how far the deck would need to be extended roughly.
Reasons agasint that option
1 - Wife wanted trees to remain to the left of the oranage line above that would have had to be removed to make room for the additional deck and cement.
2 - The deck would extend out past the house even further and the tree you see in the background has already been removed, and thought it would look more than odd from the front of the house just for stairs.
3 - A hefty price increase for additional lumber and cement for a set of stairs vs the fact that the existing stairs may have been used 2 times in 16 years.
Don't get me wrong, we thought when we first bought the place in 2005 it would be nice to have deck outside the bedroom to say have morning coffee. What we found is once you go downstairs to the kitchen to make your coffee, it's just as nice to go out and sit on the deck by a door 5' from you on the first level instead of hauling your coffee or tea back upstairs LOL
Reality is there really doesn't need to be a 3rd level deck, but as someone mentioned, it would just look odd to have a door there (I've mentioned it before, with all the windows and doors, the really does affect the heating and cooling load on the upper two levels). The only person who uses that 3rd deck is the cat, who will come down from the roof and jump on it to get the bedroom at night LOL
It was Juliet deck for at least 10 years when it was built. The contractor said he could make a pretty cool looking ladder that would give us the option of a 3rd floor "escape" in case of a fire, but I'm leaning towards Eddie's suggestion of just don't add anything. Contractor told me we could go over his idea when he starts with the wood next week.
This contractor doesn't have a company website but uses facebook, and his work looks first rate, and he seems to have a "designer" mind, and he's not afraid to offer options to spend our money LOL He's also the only contractor that told me he would not want to lay wood down so close to the ground for the bottom deck out from the basement and would only use cement for the base (he did sound like Eddie about just cutting the cement if there ever was an issue, and I guess it's just having the proper tools that you never think about because you never use them in your line of work).
All that said, I won't lie, I did think your "Fireman's pole, cargo net, inflatable bouncy thingy, zip line, knotted rope, paraglider, huge box stuffed with styrofoam peanuts" were pretty good options
I'm also VERY blessed to have this 1st world dilemma.