We are buying a house that looks like a barn! It was built in the 70s by a craftsman and truly looks like a barn on the outside--red plank siding, roof shaped exactly like a barn, sloping down on the two long sides. Very pretty in the woods. The house has some great details inside--some leaded glass, wrought iron hinges, and then some funny stuff where he ran out of time or $s such as very narrow trim, cheap carpeting instead of hardwood floors etc. We have two lists of things we want to accomplish--the little stuff above and perhaps widening the kitchen from 10 by 7 to include the closed off beautifully sunny adjacent eating area, and adding a main floor bath in an area that is a large closet, and then there are the big ideas... Intrigued by your design in "Creating the Not So Big House" where you put a second floor into a two-story greatroom (but left the mostly floor to ceiling window visible on both floors..pic on pg 11)...we want to know some recommendations on this. We could use the space upstairs--as either a bedroom or a sitting room once the kids leave--and it's big space--16 by 26. We want to maintain the integrity of the barn/crafts styling, and the view from the window is north of woods and then a house perhaps 20 yards away. Is this affordable? In buying the house we both loved the greatroom's window to the woods, but felt odd by the tall ceiling and overhanging hallway/railing that runs along the length. We have 3 teenagers, one nonprofit artist's income...perhaps we should focus on other ideas like college! We have a friend architect coming to see it (who is familiar with your work) and we'd like to have an idea of some of the things we might ask her or talk about.
You have a lot of very good questions here, which would be best answered by an architect. Sarah recommends that you hire one for an hour or two consultation. They can help you sort through what is possible and what can be done later, and to what extent. Then you can decide whether to hire them to help you with the design.
You can find an architect that practices in your area by going to the home professionals directory on this site.