Maximizing resale value here is putting away the plans and moving. You are planning a very expensive remodel here that you will NEVER recoup the costs from. Which is OK if you plan to live there long term or are willing to pay for the increased livability as an expense and not an "investment". But, be very very sure you completely internalize that statement before moving forward with your plans.

It's very traditional ... they put their money where it could impress people. That's why you find oak in LR/DR and fir or pine in bedrooms. A 3-story house from the 1880s had carved walnut or cherry paneling and stairs from ground floor to second, lovely hardwood floors. It was POSH! Second floor master and guest bedrooms and an office (even the 188s houses had home ofices) was nicely paneled and floored in oak with oak stairs leading to the servants and children's quarters on the third floor. Third floor was all painted pine. What I found amusing about the oak stairs was that the oak vanished as soon as it was out of sight of the floor the stairs started on ... the adults saw a nicely carved oak stair, but around the corner behind the dividing wall it went to pine. The lower set of stairs, of course, were fancy all the way up because the master and his guests saw the whole staircase. Servants stairs from third floor to second floor and to kitchens were painted pine.

I have a single inswing Marvin french door with transom in my brownstone parlor kitchen. They are made with an integrated frame so the seal is pretty good and less draft/heat/cold issues than I expected. They are made to order so you can order them to fit your brick opening. Although I looked into having a screen (retractable or outswing) I never bothered. The door is open a lot all summer without much of a bug issue. IIRC, your kitchen is tight and an outswing might suit you better. I didn''t need an operating transom but that might address your desire to "open" a window. Or you could just open your dining room windows - your kitchen is totally open to it. Go to some window dealers with big displays - not HD/Lowes - and take a look at the door displays.

The practical definition of a Juliet balcony is a deck that doesn't have a platform, only guard railings. The code interpretation issue is whether or not the exception to R311.3 that allows a landing less than 36" in the direction of travel is satisfied with a dimension of 0". The next question is what dimension would be allowed (2", 4", 6" etc.) I suspect you will find that your contractor knows what he is talking about. You won't be the first person to ask the building department for an interpretation of the exception to R311.3 and you may be successful but the only thing that is certain is that they cannot refuse the 4x6 deck the contractor proposed and they might accept brackets down to the existing foundation that would avoid foundation piers. They might also accept a 3x3 deck. The biggest waste of money would be the construction of two foundation piers that would later be abandoned. Ask your contractor if brackets to the foundation would reduce the cost of a 4x6 deck. If so, that might be the best solution. The contractor's offer to install the ledger board is a sign of good faith. Make sure it is through-bolted and properly flashed according to the new more strict code requirements added to the IRC after so many fatal deck failures. I recommend Grace Vycor Plus under the building wrap and over the top of the pressure treated ledger board and that should be protected with metal flashing (no unfinished aluminum). Metal flashings do not weather well when in constant contact with water on top of a ledger board so the vycor will prevent water intrusion when the metal flashing inevitably fails. the metal is essentially protecting the Vycor from UV rays. I stopped using ledger boards 40 years ago even for decks close to the ground. I always use Maine Deck Brackets.