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Well, a lot of people come to Madison for the same reasons and experience sticker shock. Since many major cities are so outrageously expensive, people know that rural areas and smaller cities, especially in the midwest, are dirt cheap. Well, Madison is the exception. While not a mini Boston or NYC price wise, a 150K house in Madison is not going to be easy to find. If you did come across something that cheap for a single family house, there would have to be some major drawbacks such as upkeep, maintence, location...in short, it would not provide or hace reasonable access to all of the reasons that would make you want to live here.
I would recommend raising your price limit by 50K...and you would greatly increase your options. If that is not possible, consider older housing on the east, northeast and south sides. Some of these areas are sketchy, but it is on a block by block basis and you could find a nice fixer upper or diamond in the rough in your price range. Fortunately, even in Madison's less than perfect areas, most homes are well kept and there is a general feeling of cleanliness and community support. No real urban ghettos to speak of...just a couple of scattered bad blocks and apartment complexes that give the neighborhoods a bad name.
The suburbs also offer more affordable housing, if that would be a consideration. Monona comes to mind...
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