I think that back bedroom would end up being too small the second way. As it would probably be about 5'8 at the narrowest end. The house is worth more with private access for both bedrooms as stated. Check with an estate agent. Just go with the landing on the left and leave the staircase. Save the pennies for something that will also add value, and that is, taking down the wall that divides the kitchen, getting rid of the downstairs loo ( unnecessary in a two up two down ) Open up the kitchen, put french doors in from the dining room to the kitchen so that you can have them open and see the whole length out to the garden if you want, , bi-folds out to the garden etc

Completely agree that there are no hard and fast rules. We've done many projects that use oak for both the flooring and the stairs. A good way of breaking it up may be to go for tiles what was your reasoning for not considering them before? It can often be a throwaway comment by friends who similarly cannot envision what the finished look can be. If they aren't a professional with your overall 'look' and 'feel' constantly in mind I would often take their opinion with a pinch of salt.

I'd say oak on oak would be a bit much. Pattern flooring ie herringbone/chevron ect seems to go nicely with oak staircases. A white oak herringbone I think would finish it off beautifully. You could have the herringbone moving into straight plank in the other rooms if it would be too much to do it all over. Pics below don't have an oak stair case but i think the colour would work

Whaou your current staircase is lovely! So stylish and different. Very unique. I do realise it is not what you want to hear :) but honestly, maybe consider keeping the railing, rather than going for glass? It give so much more characters to a house vs all modern staircase.... If new and glass it is, then I agree that pin+glass would not work. Maybe stain it/paint to match your doors, so you have an harmonious feel? I think it may look nicer and more coordinated than with the oak cladding. The cladding is unlikely to match exactly your floor too so I would worry that it would clash. If your are not considering keeping your current railing, please do consider selling/donating them (EBay or Freecycle) as they are too lovely to be going to the tip ;)