Yes but its not just the desired look. If cost is not a factor, anything is possible. But if you have not done a lot of remodeling, you may not be aware of all the associated costs with changing all this. The ceiling, the lighting, framing out the window and wall, matching and replacing the existing exterior. While maintaining the exterior design balance. Moving plumbing, gas and electrical. Your house was built for this kitchen so everything you are considering has major expense to change. You might be better off as far as function and design to bump out the back and redo the whole thing.

To piggyback on Virgil's comment...could you design the empty nest space on one floor with separate climate zones so that later on you can completely close off part of the house unless you have guests. This makes perfect sense. Specifics I'd care about: - Place everything you and your spouse will need once you're "empty nesters" on the first floor ... and make sure it's elder-friendly. - This is an ugly thought, but it's realistic: It's easy to consider you and your spouse living in this 4000 square foot house together as empty nesters ... but one day one of you will be widowed. Will 4000 square feet still feel okay then? - Put the kids' bedrooms upstairs, but make sure you can close off that space when no one's using it. Be sure you have at least one bedroom that can hold at least a queen bed so that visiting adult children (who bring along a spouse) can be housed comfortably, and think about a room that could become a grandchildren's room. - This upstairs space might one day be needed for a live-in caretaker (who could be a child or grandchild, or could be a paid caregiver). - Lose the loft and instead make the basement a kids' hang out space. - A completely different thought: Design the house so that you have two bedrooms upstairs for your younger children ... and a one-bedroom apartment (with a separate entrance PLUS a lockable connection to the main house) for the older boys. My mom has this set-up in her house, and it has proven itself very flexible over the years. In her case, the one-bedroom apartment is connected to the main house with a breezeway. Initially an elderly relative lived in the apartment. Each of us kids took turns living in that bedroom. It's been temporary housing for a number of people. Now my mother lives in the apartment, while my brother and his family have the main house. Heck that double bedroom might not even get a year or more out of it before the boys are off to college. I say that because it may be another year or two before the house is built. Yes, realistically, the oldest boys will barely ever live in the house ... but assuming they're going away for the traditional college route, they'll be home for holidays and summers. They may or may not come home after college, but they're not likely to stay long. My oldest has been out of college two years now, and as I think about her high school classmates, only one is still living at home with her mom ... and it's because she is a single mother. I know plenty of empty nesters living in 4000+ sq.ft. houses and none of them are overwhelmed. Eh, I bought my current 2400 square foot house from an empty nester who was overwhelmed both with the upkeep and the cost of the home. I know a couple other people who would like to downsize ... but they can't unload their large houses and/or can't find something small and manageable for the same cost now. I do know one retired guy who stocks grocery shelves part-time literally because he can't afford his oversized house ... neither can he sell it. As for maintenance and upkeep, well, if one can afford to build such a house, they will probably still be able to afford it 30 years later. And also afford the help to clean it. Totally disagree. Speaking hypothetically, definitely not pointing at the OP, whose financial situation I don' t know: pretty much anyone can borrow to build a big house ... but that doesn't mean the individual can afford to retire AND maintain the big house. No one wants to discover too late that he cannot afford to travel, etc. in retirement because of the necessity of maintaining a big house. I have always told my husband that I wanted a home where all the kids would have a bed to sleep on when they chose to come back home to visit. Yes, I always want to have a space for my kids ... but at 4000 square feet, you have space for other people's kids too. Remember that an average house in America today is 2400 square feet; you're looking at practically double that size. I agree that's important too, but a few thoughts on that. How many will be moving far from home and how many will be staying with you at the same time? This is more unpredictable than your own health. With four kids, will they live nearby and visit but never stay the night? will they move far away? will they likely come back to visit at the same time? will they send their kids to stay with you two weeks every summer? Other thoughts: - That's a lot of garage for anyone. - I like the connection between the laundry and the master closet. - The master bath could use improvement. - You're devoting a huge amount of space to bedrooms ... but not nearly as much to eating space. Fast forward a decade or two: imagine four children, spouses and grandchildren ... you don't have anywhere to feed even half that group! And, in my experience, you're more likely to have family for a day /a meal than for overnight. - The placement of the toilet in the shared bathroom seems to be very much "out in the open". I get that this bathroom is designed for sharing, but it could be better.

Before I became a custom home designer/builder/remodeler, I worked as a project engineer on various commercial construction and renovation projects. Suffice it to say I'm familiar with both commercial and residential construction, the trades which work in each, and the quality levels. Whether a commercial contractor is an appropriate choice for your project depends on a couple of considerations including the project size/scope, schedule, cost, the contractor's relevant experience, and your quality expectation. In general, commercial contractors deal with larger scope (e.g., really large new home construction projects), fast-track, and high-cost projects. The quality of construction is likely to be on par with entry-level or maybe move-up residential construction--not high-end residential. Schedule and cost trump quality in the commercial construction world. I don't think the commercial contractor's restaurant construction experience is all that transferable to your project. Frankly, new residential construction is different enough from residential remodeling that I would be concerned if a custom home builder wanted to bid on your project as his/her first foray into the wonderful world of remodeling. Proceed with caution.

It does not look inviting or as cared for as the rest of the property. First I would remove the guard rail on the side of the staircase and replace it with a long raised planter that fills the whole bed (I see the smaller black planter you have there now). Plant it with a low growing dense shrub to form a low wall- cheap and will feel less enclosed while still preventing people from falling into the staircase. Next I would remove the short section of railing on your deck then build a new ipe wall to match your other ipe walls from the basement landing all the way up to where the deck handrail had been. Maybe integrate lights and signage so it looks like you are supposed to be here.