your roof appears to have various angles and shapes with eaves for some parts and not others and the flat roof at the rear could be a wasted opportunity for an upstairs deck and this may be intentional but i suggest that the best roof would be determined by orientation and climate..a copy of the floor plan showing direction of north would help understand the roof better

I was thinking of options , and basically Kates sketch would be along the lines of what I am thinking . Just some obvious things -- you have a chimney -- do you want that in your Master ? You want doors off the front Den -- no matter what you do , that will cost reasonable $$$ , as you will have to alter the framing , maybe electrical , as well as obviously cutting through bricks . Could 'just' having screens and maybe even a small roof creating a courtyard in front , using the existing front door and probably creating a better entry experience if done right , be better than that ? Same with things like having an external door from a laundry/mud room ? If that was important , personally I'd incorporate that as part of the new addition at the rear -- its way easier to design framing and walls with a door included , as opposed to modifying a 60 year old building . Basically , we could question every room , and that is what the designer should have done . Without asking , I'd come up with a totally different design , but it would be what I would do , and maybe wouldn't be what you want . And as far as adding upstairs , again personally I wouldn't . Engineering wise its difficult , matching styles is difficult , and cost will be quite a bit more per metre than adding on the rear , but you may feel the advantages outweigh the costs -- only you know .

I would re-evaluate my brief, my budget and my site. It is another case of trying to squeeze too many rooms into too small a space and compromising the living space. If you draw furniture to scale in your living room then you will see that it is undersized for a four bedroom home. With the best orientation going to the garage door and bedroom 4 I would look at a complete redesign by pushing some of the bedrooms to the rear, and a central courtyard to give you an opportunity for north facing light to a living room. There is nothing nice about the current design and will feel like an apartment with little resale appeal. The designer has shown no flair or imagination in this "gun-barrel" floorplan, and is a variation on a concept that has been around for centuries. But your biggest problem is the number of rooms. Do you really need 4 bedrooms plus a study and 2.5 bathrooms, a long wasteful hallway, and only one modestly sized open plan living area and kitchen on a narrow block? I would start again with a smaller brief and a designer who can challenge your thinking about what good small house design actually means. Small house design is the hardest to do really well, so don't use a large house designer. Dr Retro of Dr Retro House Calls and Dr Retro Virtual Visits

So if you can’t install a another beam to make it look the same either side of support pillar, then that will look unfinished as well. Can you spend some money and get a beam to stretch across the space and redirect the wiring? This will cost a fortune, so I am back to a console table with a slightly wider finished support pillar, that looks as though it was meant to be there.