If you have friends and family who are willing to help, and you plan on doing a substantial amount of DIY, it can be done, but plan on living in a construction zone for a very long time. We added on a story-and-a-half (to match the bungalow style) seven years ago--360sf downstairs, small entry overhang with a patio, and a bedroom above, breaking through the existing roof where a knee-wall closet had been. We paid a local contractor to do the framing and finish the outside, except for painting (which my mother, sisters, and I did--we actually painted the whole exterior). IIRC, the contractor's fee was about $25,000--and did not include electrical, which we bartered with a neighbor who is a master electrician. We gradually finished the inside ourselves--and I do mean gradually--I just finished the bedroom last November. Here are my ideas, including some notes. You might not like them, but you asked WWYD? For that budget I'd compromise, choose the important things--and also consider what will be important in the next 10-15 years while your younger children are still living at home. I'd turn the LR on the left into a first floor bedroom, moving the entry to the other side, which will be the LR/TV room. The master in my house is on the first floor (front left), with kids' rooms upstairs, and I love it. Soon your little ones will be spending more time in their rooms, and with a bedroom downstairs, aging in place, for you, is an easier transition. I might also cantilever a closet with a shed roof, but I don't know if that would meet code in your area--bungalows often had a cantilevered bump-out along the side. The alternative is to leave the LR on the left side and put the bedroom on the right, where it seems that a bedroom was once located--it already has a closet, and the entry would not need to be changed. Then there is no option to have an entry to the bathroom, but it's just across the hall. The bath is expanded, with stacked W/D sharing plumbing. Can the dryer be vented with the bathroom vent? Other than building in the back porch and BR above (see next photo), and running new plumbing/electrical, construction is mostly moving doors, adding walls, and finishing, which can be DIY. I've noted some options--new back entry, opening between DR and LR--since we don't have a lot of info about which kind of plan you'd prefer. Also, you didn't note how much of the new kitchen you want to keep and/or re-use. Click to enlarge: On the second floor, I've added a small bedroom over the enclosed porch, and made the bathroom a full bath, which makes the existing bedroom smaller, but closer in size to the new bedroom--less fighting between daughters. ;) I've noted small doors to access storage in the eaves, and made a nice closet along the right side, for extra clothing storage. Alternately, you could increase the size of BR#3 (red rectangle), by building it out to include a cantilevered overhang, over the downstairs porch entry (porch will be enclosed). That BR could be a sleeping room for both girls, with their closets along the right side wall. Bedroom #2 would still be yours, and the LR and TV rooms downstairs would both be in the front of the house. Another idea, suited to an older home: I've thrown a lot of ideas at you--some might be helpful, some might be crazy, but trying to remodel an older home requires some work-arounds. ;) For more ideas, you can post in the Kitchens forum--some of the folks who post there also like to do whole-house layouts. And, you can post in the Smaller Homes forum for support from like-minded people. As Greendesigns suggested, it might be better to consider moving, rather than invest in changes that aren't ideal. Good luck!

We have a bedford stone house with chocolate brown soffit, fascia and gutters. The windows are trimmed in white. I am trying to figure out what color to paint the concrete lapboard siding. I really like blues, but I'm not sure what shade would work. But, I am open to other colors as well. Please let me know your ideas!!

@Classic Structures Inc. I live in the bay area. My wife is in Portland right now. If she can pick it from a store, that'd be great.

You have to paint Brown color for the roof and light cream for the bricks if you want an antique look because you putting in question you love the antique look you have to paint the gray color for the bricks and Light cream for the roof.