Thanks so much, this definitely helps. I guess the issues we want to address are exterior painting, cleaning up the roofing, making the living area open plan, sorting out 3 bathrooms and 1 kitchen, flooring, and possibly a skylight in a dark area of the house, so your above guidance definitely makes that order clearer.

You start with a Design Master Plan first. If you don’t, you end up backtracking and spending more money. For instance, it looks like dormers could be added and the attic be habitable. Is that on the list? If so, that needs to be done at the same time as the roof. Have you lived through a rainy season yet? You want to be sure that the water drainage and water flow around the house doesn’t come IN the house before you think about doing landscaping for it.

In addition to all the good advice already posted, I would suggest developing a landscaping plan early in the game. This is because it typically takes three years before it starts to look good, at least around here.

Thanks Nancy, I was wondering about landscaping. Would we paint the exterior before or after landscaping? And if we have a boundary fence put in, would we do that before or after house exterior painting?

I see no one else has mentioned windows, but, I would want to make sure windows dont leak. Its a good idea to start on the exterior, to make sure, the house stays dry. I wouldnt want to redo the interior and then find out you have water penetration somewhere.

If you are going to paint the exterior, I would do it before planting anything near the house. but it would be good to get a Landscaping plan established as soon as possible. you might find out for example that the lawn needs some regrading near the foundation. That would be a high priority, as it relates to drainage and keeping a dry basement. A fence could be put in any time, but you should consider it in relation to the Landscaping plan.

making the living area open plan

This is likely to be the most expensive, most complex, and most life-disruptive part of your project. It's also not likely to return its cost in increased value when you sell the house.

If your house's architect didn't design it to be open, parts of the house will effectively have to be re-engineered. You'll need the services of a structural engineer.

Unless you got your house for a price well below market value, you're probably better off selling it and buying one that already has the layout you really want.