Hi Brooke If then plan is to fully renovate then go for it...! It will be just fine. A new finish on the floor will lift it too. Doing the floor before the skirting boards will save skirting getting damaged and having to touch up paint. You can find a white to go with your grey by reducing the grey down untill its white then you won't have clashing undertones. Other wise check with your paint store for the whites to compliment your grey choice. :)

some of the older carpenters and cabinetmakers will have the necessary traditional planes for cutting these profiles or you could have one made out of plaster, cement.or builders bog moulded out of a cast made from the remnants of the original board or try a high tech solution with a copy made with a 3D printer or two separate lengths of moulded timber attached together to approximately match the original but you'll need to research plaster works, restoration companies, specialist carpenters and tech colleges for a computer, woodworking or art student keen to try an interesting project but you may find that it's quicker and easier to replace the whole section with an unmatched section of plain skirting board or try stealing a section from somewhere else in the house where the skirting board is hidden behind a bed or lounge and replace the hidden area with the plain board...best of luck with your repairs

I would prefer to see both ceilings matched with shiplap, to help tie the space, we all tend to look up. This would also mean that the wall between both rooms can be removed and therefore make the room appear bigger, as the height of the ceilings in each room will make them appear smaller if the wall isn't removed

Thanks so much for the comments. It’s literally cutting & installing the skirting boards only (no architraves) and we are providing the boards already painted (5.4m lengths). It will be a clear run as it‘ll be right after the new floors are laid so no furniture around at all. Quite a lot of angle cuts though. Still reasonable? I suppose it comes down to peace of mind on a quality job or take a punt on a handyman (unfortunately don’t know any so would have to take a chance). Oh dear, wish the budget wasn’t so tight otherwise I wouldn’t hesitate.