Hi everyone, Thanks for the responses. It's been more than four months since my original query so I thought I'd post an update. After talking with several other contractors and vendors, we decided that going with replacement windows was clearly the wrong choice, so we switched contractors to someone with more large-scale remodeling experience and went with new construction windows. In the end we chose Anderson 400s and used Azek trim on the outside. The old windows came out and we found some damage to the underlying sheathing and framing, but not too much. The new windows were installed and insulated properly and the difference is huge. While we were at it we also replaced most of the edge and corner trim and drip caps on the house as this was rotting off as well. The project is taking a lot longer (we're hopefully wrapping up this week) and is costing a lot more than we thought, but I'm glad we caught this when we did as the damage would have been a lot worse if we had waited. Interestingly, the cost of the new construction windows was actually less than the replacement windows. The labor was more, of course, but we were already being forced to replace the rotting exterior trim so that was all equal. We did have to replace the interior trim, which was not inexpensive, but in the end the project wound up costing the same because the windows were less expensive. The difference in the new trim is amazing- it's nice to have real window sills and stools, with a less generic casing around them. The question of new windows vs. restoration was never an issue- the old windows (only 18 years old) were of poor quality, poorly installed, and leaked cold air to the point that we had to install plastic sheeting over the openings in the winter. Also, many of the window sills, mullions, and jams were rotting, so the amount of work to restore the existing windows would have been huge, We were going with new windows one way or the other. Thanks again for your help, Josh

Which irritates you the most -- the way the yard looks or the way the house looks? You could begin by doing any grading your yard needs and adding any concrete or gravel or pavers for your driveway and sidewalk and any retaining walls; then plant grass where you're going to want grass. Then stop work on the outside and finish the work on the inside, beginning with the indoor project that will require the most ripping out and replacing of any electrical and plumbing and heat/ac duct/vents. All that core replacement work needs to be completed before beginning any finishing work. Once you're through with all the tearing out, you can install any new flooring. Then you can get to the finishing touches such as paint and then light fixtures. Then get back to the outdoor tasks of patio, flower garden, etc.

You've got shakes and brick on the front and, what appears to be, vinyl along the side. Was the house built like this in the 1980's? If so, then just paint it all one color. Or remove the front brick and shingle and re-side. Or just re-side the whole thing in fiberboard if your budget allows. If you want to play with the roofline, then that's going to require some input from a professional (like an architect). I think painting it all one color is the answer. However, I am reading a book on Bungalows and Craftsman homes and they painted the upper and lower floors different colors specifically to make the homes appear lower and wider. So maybe that's an option--but you don't have a visual divider between the 2 floors on the sides so, again, I would just go with all one color. You don't need to make it look less like a dutch colonial, you just need it to look like the prettiest Dutch Colonial. You need nice landscaping.

Update. Wanted to come back and thank everyone here who gave feedback. We made many of the changes you suggested. The advice to simplify and to minimize the vertical lines was spot-on! We removed half of the posts, filled in the recess above the roof over the front door (what was that anyway?), used just one siding material (Hardie plank), and painted the corner trim the body color instead of the trim color. It was too late to change the roof or even to connect the roofs over the front and mud room doors, since they are different pitches. Body has been painted SW Pewter Green. Trim is SW Gossamer Veil. We should be able to take pics here in the next couple days.