I live in a house built in the 1940's, and the first thing that jumped out at me from your post was wanting a big island. In a lot of older houses, open plan kitchens with islands are possible only if you take down load-bearing walls and completely rework the layout and flow of the house. In other words, if you want a kitchen with a big island, you might be asking something of the house that it was not designed to have. It can be done, but sometimes it means more trouble and expense than either buying a house that was built with a big open kitchen in the first place, or modifying your vision of the kitchen to fit what the house already has. Of course you might find an older house that already has the kitchen layout you want. That would be easiest! But if you don't find one, keep an open mind. Islands serve a function in some layouts but aren't needed in others. Our kitchen doesn't have an island or a peninsula, but with two sinks and two prep areas, it works for multiple cooks. The only other advice I have is to ignore everything about surface design right now and concentrate on layout and logistics. Don't decide yet on painted vs stained cabinets or what kind of countertops you want; you can have those in any house. Try not to be swayed by how charming a kitchen looks, if you're going to be taking it out anyway. Look at traffic flow, positions of doors and windows -- are the windows too low to put a countertop in front of? -- ceiling heights, etc. If you're looking in a neighborhood with historic designation, there may be limits on what you can do. And be aware that you might have to include lead and/or asbestos abatement in your budget. Good luck and have fun looking! I make it sound kind of grim, but I like living in an older house and I would love (most days) to live in one from the 1910's or 20's!

thanks for the thoughts, I guess I should have said fenced yard, or yard appropriate to being fenced, not all are. One more question for you about lot layout, just to get some outside thoughts: The house is back from the street with a large front yard as was becoming popular when it was built (110x300 ft lot) with the house roughly in the center judging by google maps overhead view. On one hand I don't want to be right on the street as I am now (the edge of my porch is 13 ft from the edge of the sidewalk, back yard is about 175 ft deep now), meaning the proposed house while on a larger would have a similar sized (slightly larger) functional back yard as I have now (not as deep, but somewhat wider). So I guess what I am trying to ask is, do you think that this lot layout is too wastefull with a big front yard, assuming under utilized front yard, and am I over compensating for the lack of front yard I have now? (optional reading paragraph-->) The house on the north side is about even with the one under consideration and the one on the south side is on an even deeper lot and sets back much more, with the front of that house probably 250 feet from the street, almost even with the back of the property I am considering, it is also offset farther to the side than would be suggested by lot dimensions as there is also space for a never built (and never will be) street right of way between them.

The two main things to consider are whether the soil is solid enough to support the total weight and then whether the existing structure is strong enough to support the added weight. I used to live in a pier/beam house built on solid limestone. Two stories on solid rock is a simple calculation. Now I live in a slab based house built on fill dirt on top of solid limestone. Adding a second story to this house would require some soil testing.

Our last house needed everything. The roof was four layers thick with the last one put on over thirty years before we bought the house. It still had knob and tube wiring. It had zero functioning appliances—even the heat did not work. One of the two bathrooms had a leaking shower. And on and on. But it was the perfect location (great schools in walking distance, walk to library, walk to movies, walk to shops and restaurants, easy access to commute routes, adorable neighborhood). It was the right size and had the best curb appeal ever. And there was very very very little on the market. We spent three years and a lot of effort and money fixing everything. And then about a year after finishing our last project, we moved. Sigh. Our housing market was hot so we sold for enough to cover the money we put in plus more, but that’s not quite the same as getting our money back because I am sure we could have done nothing and still sold for more than we paid. So if you hate remodelling ( I actually like the planning part quite a bit, but not the living in the under construction house with kids part at all), I would think carefully about taking on a huge project.